1,3,4-thiadiazoles useful for the treatment of CMV infections

ABSTRACT

The present invention presents novel 1,3,4-thiadiazole derivatives of formula I ##STR1## which have useful antiviral activity against herpes virus, cytomegalovirus (CMV).

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of provisional application U.S. Ser. No. 60/078,528, filed Mar. 19, 1998, under 35 USC 119(e)(i).

BACKGROUND OF THE INVENTION

The present invention relates to novel 1,3,4-thiadiazole derivatives having useful antiviral activity against herpes virus, cytomegalovirus (CMV). The invention also relates to a pharmaceutical composition containing such compounds and methods for the treatment of such viral infections. Many of these compounds are also active against other herpes viruses, such as the varicella zoster virus, the Epstein-Barr virus, the herpes simplex virus, and the human herpes virus type 8 (HHV-8).

INFORMATION DISCLOSURE

Derwent Abstracts 07484C/05 discloses 2-acylamino-1,3,4-thiadiazole derivatives useful as pesticides, optical brightening agents, and intermediates for pharmaceuticals.

Derwent Abstracts 46012X/24 discloses anti-inflammatory composition containing 1,3,4-thiadiazoles derivatives as active agents.

J. Chem. Soc. (C), Vol. 13, 1813-1823, (1970) describes addition-cyclisation reactions undergone by aroyl isothiocyanates with NN'-diaminoguanidines.

J. Heterocyclic Chem. Vol. 25, 1071-1074 describes a new route to 1,2,4-triazoles and 1,3,4-thiadiazoles from 1-acylbithiourea.

SUMMARY OF THE INVENTION

The present invention provides a compound of formula I ##STR2## or pharmaceutically acceptable salts thereof wherein: Y is

a) --NHR₁, or ##STR3## X is --O--, --S(═O)_(h) --, --CH₂ --, or --NR₂ --; R₁ is

a) C₁₋₁₈ alkyl,

b) --(CH₂)_(i) --C₃₋₇ cycloalkyl,

c) --(CH₂)_(i) -bicycloalkyl,

d) --(CH₂)_(j) -M,

e) --(CH₂)_(j) -W,

f) --(CH₂)_(k) aryl, wherein aryl may be substituted with one to three R₃,

g) --(CH₂)_(k) -het, wherein het may be substituted with one to three R₃,

h) --(CH₂)_(k) -Q, wherein Q may be substituted with one to three R₃, or

i) H;

R₂ is

a) H,

b) C₁₋₄ alkyl,

c) --C(═O)C₁₋₄ alkyl,

d) --S(═O)C₁₋₄ alkyl,

e) --CO₂ C₁₋₄ alkyl, or

f) --CO₂ CH₂ phenyl;

R₃ is

a) halo,

b) C₁₋₄ alkyl,

c) C₁₋₄ alkoxy,

d) benzyl,

e) --CN,

f) --SO₂ F,

g) --SO₂ NH₂,

h) --CF₃,

i) --NO₂,

j) --OCH₂ O--,

k) --CO₂ (C₁₋₄ alkyl),

l) --C(═O)C_(l-4) alkyl,

m) --C(═O)NH₂,

n) --NHCO₂ (C₁₋₄ alkyl), or

o) --C(═O)--O--C(═O)--;

M is

a) --CN

b) halo,

c) --CO₂ C₁₋₄ alkyl,

d) --CH(phenyl)₂, ##STR4## W is a) --OR₄,

b) --SR₄,

c) --NHR₅, or

d) --NR₆ R₇ ;

R₄ is

a) C₁₋₄ alkyl,

b) C₃₋₇ cycloalkyl, or

c) aryl,

R₅ is

a) C₁₋₇ alkyl,

b) C₃₋₇ cycloalkyl,

c) aryl, or

d) --C(═O)C₁₋₄ alkyl;

R₆ and R₇ are independently

a) C₁₋₄ alkyl, or

b) R₆ and R₇ together with nitrogen form a 4- to 6-membered saturated heterocyclic moiety having one to two atoms selected from the group consisting of oxygen, nitrogen, and sulfur;

R_(x) is

a) C₁₋₁₈ alkyl,

b) C₂₋₁₈ alkenyl,

c) C₂₋₁₈ alkynyl,

d) C₂₋₆ alkyl substituted with one to three halo, C₁₋₃ alkoxy, --OH, --SH, or --CO₂ H,

e) C₂₋₆ alkenyl substituted with aryl, wherein the aryl may be in turn substituted with one to three R₂,

f) --(CH₂)_(i) aryl, wherein aryl may be substituted with one to three R₃,

g) --(CH₂)_(i) -Q, wherein Q may be substituted with one to three R₃, or

h) --(CH₂)_(i) -U, wherein U may be substituted with one to three R₃ ;

aryl is phenyl or naphthyl;

het is 5- to 10-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur;

U is 5- to 9-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur;

Q is 5- or 6-membered saturated heterocyclic moiety having one to two atoms selected from the group consisting of oxygen, nitrogen, and sulfur, wherein nitrogen atom may be in turn substituted with C₁₋₄ alkyl, phenyl, benzyl, --C(═O)C₁₋₄ alkyl, or --CO₂ C₁₋₄ alkyl;

h is 0, 1, or 2; i is 0, 1, 2, 3, or 4; j is 2, 3, or 4; k is 0, 1, 2, 3, 4, 5, or 6;

and with the following provisos:

a) where R₃ is phenyl or 4-methoxyphenyl, R₁ is other than phenyl, 4-methoxyphenyl, or 4-chlorophenyl;

b) where R₃ is --CH₂ phenyl, R₁ is other than phenyl or --CH₂ phenyl;

c) where R₃ is H, substituted or unsubstituted alkyl or phenyl, R₁ is other than unsubstituted alkyl or phenyl.

The compounds of the present invention have antiviral activity against cytomegalovirus (CMV), a member of herpes virus.

DETAILED DESCRIPTION OF THE INVENTION

For the purpose of the present invention, the carbon content of various hydrocarbon containing moieties is indicated by a prefix designating the minimum and maximum number of carbon atoms in the moiety, i.e., the prefix C_(i-j) defines the number of carbon atoms present from the integer "i" to the integer "j", inclusive. Thus, C₁₋₄ alkyl refers to alkyl of one to four carbon atoms, inclusive, or methyl, ethyl, propyl, butyl, and isomeric forms such as, for example, straight and branched form thereof.

The terms "C₁₋₄ alkyl", and "C₁₋₁₈ alkyl" refer to an alkyl group having one to four, or one to eighteen carbon atoms respectively such as, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl and their isomeric forms thereof.

The terms "C₂₋₁₈ alkenyl" refers to at least one double bond alkenyl group having two to eighteen carbon atoms, for example, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, heptenyl, octenyl, octadienyl, octatrienyl, nonenyl, undecenyl, dodecenyl, etc., and their isomeric forms thereof.

The term "C₂₋₁₈ alkynyl" refers to at least one triple bond alkynyl group having two to twelve carbon atoms such as, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, octadiynyl, octatriynyl, nonynyl, nonediynyl, etc., and their isomeric forms thereof.

The term "C₃₋₇ cycloalkyl" refers to monocyclic hydrocarbons having three to seven carbon atoms such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and their isomeric forms thereof, preferably an cycloalkyl group having three to six carbon atoms.

The term "bicycloalkyl" refers to saturated alicyclic hydrocarbon systems consisting of two rings only, having two or more atoms in common.

The terms "C₁₋₄ alkoxy" refers to an alkyl group having one to four carbon atoms attached to an oxygen atom of hydroxyl group such as; for example, methoxy, ethoxy, propyloxy, butyloxy, and their isomeric forms thereof.

The term "aryl" refers to monocarbocyclic or bicarbocyclic aromatic moiety such as; for example phenyl, naphthyl, biphenyl. Each of these moieties may be substituted as appropriate. Aryl is preferably phenyl or phenyl substituted with C₁₋₄ alkyl, C₁₋₄ alkoxy, halo, --CN, --SO₂ NH₂, --SO₂ F--, --NO₂, --C(═O)--O--C(═O)-- or --OCH₂ O--.

The term "het" refers to a 5- to 10-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur such as, for example, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl, indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, isoindolyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl or cinnolinyl.

The term "U" refers to 5- to 9-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur such as, for example, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl, indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, or isoindolyl.

The term "Q" refers to 5- or 6-membered saturated heterocyclic moiety having one to two atoms selected from the group consisting of oxygen, nitrogen, and sulfur, wherein nitrogen atom may be in turn substituted with C₁₋₄ alkyl, phenyl, benzyl, or --C(═O)C₁₋₄ alkyl. The example of Q is 2-, 3-, or 4-piperidinyl, 1-, or 2-pyrrolidinyl, morpholinyl, thiomorpholinyl, dioxolanyl, imidazolidinyl, oxathiolanyl, oxazolidinyl, tetrahydrofuryl, or 2-oxo-1-pyrrolidinyl.

The term "halo" refers to fluoro, chloro, bromo, or iodo.

The term "pharmaceutically acceptable salts" refers to those salts which possess the biological effectiveness and properties of the parent compound and which are not biologically or otherwise undesirable.

Throughout this application, abbreviations which are well known to one of ordinary skill in the art may be used, such as "Ph" for phenyl, "Me" for methyl, etc.

Examples of preferred compounds of the present invention are:

1. N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,

2. N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

3. N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

4. N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

5. 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,

6. N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

7. 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,

8. N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

9. (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,

10. 2-ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,

11. 2,6-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,

12. N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,

13. N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,

14. (E)-N-(5-{[4-(aminosulfonyl)benzyl]aminol-1,3,4-thiadiazol-2-yl)-9-octadecenamide,

15. N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,

16. (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,

17. 2,6-dichloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,

18. 2,6-dichloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,

19. (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,

20. N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2,6-dichlorobenzamide,

21. 2,6-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2yl)benzamide,

22. 4-cyano-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,

23. N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

24. 4-cyano-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2yl)benzamide,

25. N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-5-nitro-2-furamide,

26. 2,6-dichloro-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]benzamide,

27. 4-cyano-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,

28. N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

29. N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6-dichlorobenzamide,

30. N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide,

31. (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,

32. (E)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,

33. (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,

34. (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,

35. (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,

36. 2,6-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, or

37. N-(5-{[4-(aminosulfonyl)benzyl]amino-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide.

Examples of more preferred compounds of the present invention are:

1. N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,

2. N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

3. N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

4. N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

5. 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,

6. N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,

7. 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,

8. N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, or

9. (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide.

The compounds of the present invention and pharmaceutically acceptable salts thereof are useful as antiviral agents. Thus, these compounds are useful to combat viral infections in animals, including man. Specifically, these compounds have anti-viral activity against the herpes virus, cytomegalovirus (CMV). Many of these compounds are also active against other herpes viruses, such as the varicella zoster virus, the Epstein-Barr virus, the herpes simplex virus, and the human herpes virus type 8 (HHV-8).

Also, while many of the compounds of the present invention have shown activity against the CMV polymerase, these compounds may be active against the cytomegalovirus by this or other mechanisms of action. Thus, the description below of these compounds' activity against the CMV polymerase is not meant to limit the present invention to a specific mechanism of action.

The compounds of the present invention are tested in an polymerase assay to show activity described below, which is indicative of a compound's activity and thus of its use as an anti-viral agent.

The HCMV polymerase assay is performed using a scintillation proximity assay (SPA) as described in several references, such as N. D. Cook, et al., Pharmaceutical Manufacturing International, pages 49-53 (1992); K. Takeuchi, Laboratory Practice, September issue (1992); U.S. Pat. No. 4,568,649 (1986); which are incorporated by reference herein. Reactions are performed in 96-well plates. The assay is conducted in 100 μl volume with 5.4 mM HEPES (pH 7.5), 11.7 mM KCl, 4.5 mM MgCl₂, 0.36 mg/ml BSA, and 90 nM ³ H-dTTP. Assays are run with and without CHAPS, (3-[(3-Cholamidopropyl)-dimethylammonio]-1-propanesulfonate) at a final concentration of 2 mM. HCMV is diluted in enzyme dilution buffer containing 50% glycerol, 250 mM NaCl, 10 mM HEPES (pH 7.5), 100 μg/ml BSA, and 0.01% sodium azide. The HCMV polymerase, which is expressed in recombinant baculovirus-infected SF-9 cells and purified according to literature procedures, is added at 10% (or 10 μl) of the final reaction volume, i.e., 100 μl. Compounds are diluted in 50% DMSO and 10 μl are added to each well. Control wells contain an equivalent concentration of DMSO. Unless noted otherwise, reactions are initiated via the addition of 6 nM biotinylated poly(dA)-oligo(dT) template/primer to reaction mixtures containing the enzyme, substrate, and compounds of interest. Plates are incubated in a 25° C. or 37° C. H₂ O bath and terminated via the addition of 40 μl/reaction of 0.5 M EDTA (pH 8) per well. Reactions are terminated within the time-frame during which substrate incorporation is linear and varied depending upon the enzyme and conditions used, i.e., 30 min. for HCMV polymerase. Ten μl of streptavidin-SPA beads (20 mg/ml in PBS/10% glycerol) are added following termination of the reaction. Plates are incubated 10 min. at 37° C., then equilibrated to room temperature, and counted on a Packard Topcount. Results of the testing of compounds of the present invention in this assay are shown in TABLE 1 below.

These compounds of the present invention are administered in a pharmaceutical composition containing the compound in combination with a suitable excipient, the composition being useful in combating viral infections. Pharmaceutical compositions containing a compound appropriate for antiviral use are prepared by methods and contain excipients which are well known in the art. A generally recognized compendium of such methods and ingredients is Remington's Pharmaceutical Sciences by E. W. Martin (Mark Publ. Co., 15th Ed., 1975), which is hereby incorporated by reference herein.

The quantity of active component, that is the compounds of formula I according to this invention, in the pharmaceutical composition and unit dosage form thereof may be varied or adjusted widely depending upon the particular application method, the potency of the particular compound and the desired concentration. Generally, the quantity of active component will range between 0.5% to 90% by weight of the composition.

The compounds of the present invention are administered parenterally (for example, by intravenous, intraperitoneal or intramuscular injection), topically, orally, or rectally, depending on whether the preparation is used to treat internal or external viral infections.

For internal infections, the compositions are administered orally or parenterally at dose levels, calculated as the free base, of about 0.1 to 300 mg/kg, preferably 1.0 to 30 mg/kg of mammal body weight, and are used in man in a unit dosage form, administered one to four times daily in the amount of 1 to 1000 mg per unit dose.

For parenteral administration or for administration as drops, as for eye infections, the compounds are presented in aqueous solution in a concentration of from about 0.1 to 10%, more preferably about 0.1 to 7%. The solution may contain other ingredients, such as emulsifiers, antioxidants or buffers.

The exact regimen for administration of the compounds and compositions disclosed herein will necessarily be dependent upon the needs of the individual subject being treated, the type of treatment and, of course, the judgment of the attending practitioner.

The following Scheme outlines the preparation of the compounds of the present invention. ##STR5##

In Scheme I, Y is --NHR₁, or ##STR6## R₁ Rx and X are as defined previously. The synthesis of structures 3 and 4, the compounds of the present invention, required two or three steps. 2-Amino-5-bromo-1,3,4-thiadiazole 2 is prepared through bromination of commercially available 2-amino-1,3,4-thiadiazole. Compound 3 is prepared through direct bromide displacement of thiadiazole 2 with an appropriate amine. Compound 3 then react with an appropriate acid chloride to provide compound 4.

It will be apparent to those skilled in the art that the described synthetic procedures are merely representative in nature and that alternative synthetic processes are known to one of ordinary skill in organic chemistry.

The compounds and their preparations of the present invention will be better understood in connection with the following examples, which are intended as an illustration of and not a limitation upon the scope of the invention.

EXAMPLE 1 Preparation of Starting Material 5-bromo-1,3,4-thiadiazol-2ylamine.

To a stirred solution of 2-amino-1,3,4-thiadiazole (40.5 g) in 250 ml of acetic acid is added 22.7 ml of bromine over about 20 minutes. The flask is surrounded by an ice bath during the addition to maintain the reaction temperature near 25° C. Following the addition, the ice bath is removed and the clear red solution stirred at ambient temperature for 18 hours, then added to 1L of cracked ice. Excess bromine is quenched with NaHSO₃, and 40 ml of 50% aqueous NaOH is added. The precipitated solid is isolated by filtration and washed well with water, then dissolved in 300 ml of water containing 40 ml concentrated. HCl. The solution is filtered from a small amount of solid, then 87 g of K₂ HPO₄ in a small quantity of water is added. The resulting slurry is chilled in ice and filtered, and the solid washed well with water. Recrystallization of the product from 400 ml of ethanol provides 26.3 g of the title compound.

¹ NMR (DMSO-d₆) δ 7.51 ppm.

EXAMPLE 2 Preparation of tert-Butyl 4-(5-amino-1,3,4-thiadiazol-2-yl)tetrahydro-1(2H)-pyrazinecarboxylate. ##STR7##

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (9.27 g), Boc-piperazine (11.51 g), and K₂ HPO₄ (13.4 g) in 30 ml of DMF is heated at 100° C. under argon for four hours, then cooled and added to 100 g of ice. The mixture is extracted with ethyl acetate, and the organic phase washed twice with water and dried (MgSO₄). Following removal of the solvent under reduced pressure, the residue is flash chromatographed on silica using 4% methanol in dichloromethane to afford 8.32 g of the title compound as a solid. Recrystallization from 240 ml of 1:1 acetonitrile-toluene provides 6.65 g of solid.

¹ NMR δ 1.47, 3.34, 3.53, 4.8 ppm; IR 3411, 3132, 1698, 1676, 1500, 1427, 1251, 1167 cm⁻¹ ; EI HRMS m/z found: 285.1277; M.p. 215-216° C.

EXAMPLE 3 Preparation of N-(5-Amino-1,3,4-thiadiazol-2-yl)-N-phenethylamine. ##STR8##

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (360 mg), phenethylamine (0.38 ml), and K₂ HPO₄ (522 mg) in 2 ml of DMF is heated under nitrogen at 100° C. for two hours, then partitioned between water and ethyl acetate. The organic phase is washed with water and brine, dried over MgSO₄, and concentrated under reduced pressure. Flash chromatography of the residue on silica using 4-5% methanol in dichloromethane provides 261 mg of the title compound. Recrystallization of 238 mg of this from 10 ml of 1:1 acetonitrile toluene affords 205 mg of crystals.

¹ H NMR δ 2.92, 3.50, 7.2-7.3 ppm; IR 3186, 1565, 1505 cm⁻¹ ; EI MS m/z 221; M.p. 156-157° C.; Anal. Found: C, 54.51; H, 5.47; N, 25.26; S, 14.30.

EXAMPLE 4 Preparation of 5-Morpholino-1,3,4-thiadiazol-2-ylamine. ##STR9##

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine, K₂ HPO₄ (5.7 g), and 5.3 ml of morpholine in 20 ml of DMF is heated at 80° C. under nitrogen for 18 hours, then diluted with 50 ml of water. The clear solution is placed in a continuous extractor and extracted with a brisk flow of dichloromethane for 18 hours. The solution is dried over MgSO₄ and concentrated under reduced pressure, with toluene azeotropes to remove DMF. Recrystallization of the residual solid from 50 ml of acetonitrile and 100 ml of toluene affords 3.92 g of the title compound.

¹ H NMR δ 3.34, 3.80 ppm; IR 1528, 1499, 1448, 1245, 1112, 1036, 906 cm⁻¹ ; EI MS m/z 186; Anal. Found: C, 38.67; H, 5.48; N, 30.17; S, 17.18.

EXAMPLE 5 Preparation of tert-Butyl N-{2-[(5-amino-1,3,4-thiadiazol-2-yl)amino]ethyl}carbamate. ##STR10##

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (5.40 g), K₂ HPO₄ (7.84 g), and Boc-ethylenediamine (9.6 g) in 20 ml of DMF is stirred at ambient temperature for 18 hours. The solid paste obtained is recrystallized from 100 ml of acetonitrile and 100 ml of water to provide 6.18 g (79%) of the title compound.

¹ H NMR (MeOH-d₄) δ 1.40, 3.2-3.3 ppm; IR 2989, 1676, 1577, 1512, 1366 cm⁻¹ ; EI MS m/z 260; M.p. 219-220° C.

EXAMPLE 6 Preparation of N-[5-(Cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide.-ethoxy-1-naphthoyl). ##STR11##

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K₂ HPO₄ (780 mg), and cycloheptylamine (0.51 mg) in 5 ml of DMF is stirred at 60° C. for 4 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0° C., is added a solution of 469 mg of 2-ethoxy-1-naphthoyl chloride in 5 ml of chloroform. The solution is stirred at room temperature overnight, then concentrated under reduced pressure. Addition of water and ethyl acetate to the residue provides a solid, which is filtered, washed with ethyl acetate and water, and dried under vacuum to afford 200 mg of the title compound as a white solid.

¹ H NMR (CDCl₃) δ 1.50, 1.4-1.8, 2.1, 3.6, 4.26, 7.3-7.6, 7.8, 8.0 ppm; HRMS (m+H) 411.1875.

EXAMPLE 7 Preparation of N-[5-(Cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide. ##STR12##

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K₂ HPO₄ (780 mg), and cycloheptylamine (0.51 mg) in 5 ml of DMF is stirred at 60° C. for 4 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0° C., is added 0.30 ml of o-anisoyl chloride. The solution is stirred at room temperature overnight, then concentrated under reduced pressure and diluted with 100 ml of water. The precipitated solid is filtered, washed with water, and dried under vacuum to afford 641 mg of the title compound.

¹ H NMR (CDC1₃) δ 1.4-1.7, 2.1, 3.6, 4.09, 7.0-7.2, 7.6, 8.25 ppm; HRMS m/z 346.1469.

EXAMPLE 8 Preparation of N-{5-[(2,2-Diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide. ##STR13##

A mixture 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K₂ HPO₄ (780 mg), and 2,2-diphenylethylamine (789 mg) in 5 ml of DMF is stirred at 60° C. for 4 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0° C., is added a solution of 2-ethoxy-1-naphthoyl chloride (469 mg) in 5 ml of chloroform. The solution is stirred at room temperature overnight, then concentrated under reduced pressure and diluted with 100 ml of water. The resultant solid is filtered, washed with water, and dried under vacuum to provide 947 mg of the title compound.

¹ H NMR (CDCl₃) δ 1.43, 4.02, 4.15, 4.26, 4.44, 7.2-7.6, 7.8-8.0 ppm; HRMS (m+H) 495.1846.

EXAMPLE 9 Preparation of 2-Ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide. ##STR14##

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K₂ HPO₄ (780 mg), and tryptamine (641 mg) in 5 ml of DMF is stirred at 60° C. for 12 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0° C., is added a solution of 469 mg of 2-ethoxy-1-naphthoyl chloride in 5 ml of chloroform. The solution is stirred at room temperature overnight, then concentrated under reduced pressure and diluted with 100 ml of water. The resultant solid is filtered, washed with water, and dried under vacuum to provide 866 mg of white solid. Column chromatography of 249 mg of this on silica, using 1.5-4% methanol in dichloromethane, provides 191 mg of the title compound.

¹ H NMR (CDCl₃) δ 1.43, 3.16, 3.70, 4.26, 7.0-7.2, 7.3-7.4, 7.5, 7.6, 7.8, 8.0 ppm; HRMS (m+H) 458.1655.

EXAMPLE 10 Preparation of N-[5-({[(2R)-6,6-Dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide. ##STR15##

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K₂ HPO₄ (780 mg), and myrtanylamine (0.67 mg) in 5 ml of DMF is stirred at 60° C. for 12 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0° C., is added a solution of 2-ethoxy-1-naphthoyl chloride (469 mg) in 5 ml of chloroform. The solution is stirred at room temperature overnight, then concentrated under reduced pressure and diluted with 100 ml of water. The resultant solid is filtered, washed with water, and dried under vacuum to provide 846 mg of solid. Column chromatography of 249 mg of this on silica, using 2-4% methanol in dichloromethane, provides 220 mg of the title compound.

¹ H NMR (CDCl₃) δ 1.07, 1.23, 1.44, 1.8-2.1, 2.4, 3.3, 4.27, 7.2-7.6, 7.8, 8.0 ppm; HRMS (m+H) 451.2163.

EXAMPLE 11 The Following 1,3,4-Thiadiazoles of the Present Invention Are Prepared by General Procedure Described Below.

To each 48 solutions of 5-bromo-1,3,4-thiadiazol-2-ylamine (234 mg, 1.3 mmol) in 1.5 ml of DMF is added K₂ HPO₄ (272 mg) and 1.3 mmol of the following amines respectively: phenethylamine, 2-furylmethylamine, 1-(3-aminopropyl)-2-pyrrolidinone, 2-pyridinylmethylamine, N-(2-aminoethyl)-N-phenylamine, 2-(1H-indol-3-yl)ethylamine, cycloheptylamine, cyclohexylmethylamine, (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methylamine, 2-(1-pyrrolidinyl)ethylamine, tetrahydro-2-furanylmethylamine, 4-pyridinylmethylamine, 1,3-benzodioxol-5-ylmethylamine, 2-morpholinoethylamine, 1-naphthylmethylamine, 4-fluorobenzylamine, 3-pyridinylmethylamine, 2-piperidinoethylamine, 2-ethylhexylamine, 4-(2-aminoethyl)benzenesulfonamide, N-(3-aminopropyl)-N-cyclohexylamine, 3,4-dichlorobenzylamine, 3,4-dimethoxybenzylamine, 4-phenylbutylamine, 2,2-diphenylethylamine, undecylamine, 3,3-diphenylpropylamine, 2-(2-thienyl)ethylamine, 4-(aminomethyl)benzenesulfonamide, 3-(4-methylpiperazino)propylamine, 3-aminopropanenitrile, 2-(phenylsulfanyl)ethylamine, 2-thienylmethylamine, N-(2-aminoethyl)acetamide, 3-(1H-imidazol-1-yl)propylamine, tert-butyl 3-aminopropanoate, cyclopropylamine, cyclopropylmethylamine, 2-(1H-imidazol-4-yl)ethylamine, 2-(ethylsulfanyl)ethylamine, cyclobutylamine, 2-(1-methyl-2-pyrrolidinyl)ethylamine, 2,3-dihydro-1H-inden-1-ylamine, neopentylamine, 1,2,3,4-tetrahydro-1-naphthalenamine, ethyl 4-aminotetrahydro-1(2H)-pyridinecarboxylate, 1-benzyl-4-piperidinylamine, and N-(2-aminoethyl)-N,N-dimethylamine.

The resultant 48 mixtures are heated at 60° C. for 3 hours to provide a DMF solutions of the corresponding substituted aminothiadiazole intermediates. The solutions of intermediate aminothiadiazoles are diluted with pyridine to a volume of 10.0 ml, and solids are removed by centrifugation. The supernatants are aliquoted into wells of 96-well plates (0.40 ml per well) respectively, and to each well is added 0.26 ml of a 0.2 M chloroform solution of the following acid chlorides respectively: 2,4-difluorobenzoyl chloride, 2-methoxybenzoyl chloride, 4-bromobenzoyl chloride, 4-methylbenzoyl chloride, 5-chloropentanoyl chloride, 4-cyanobenzoyl chloride, 3-nitrobenzoyl chloride, 3,5-difluorobenzoyl chloride, (E)-3-(2-chlorophenyl)-2-propenoyl chloride, 2-ethoxy-1-naphthoyl chloride, (Z)-9-octadecenoyl chloride, 2,6-dichlorobenzoyl chloride, 3,4-dichlorobenzoyl chloride,4-(trifluoromethyl)benzoyl chloride, (E)-3-phenyl-2-propenoyl chloride, 4-iodobenzoyl chloride, 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carbonyl chloride, 4-(fluorosulfonyl)benzoyl chloride, 2,4,6-triisopropylbenzoyl chloride, 5-nitro-2-furoyl chloride, and 1-benzothiophene-2-carbonyl chloride.

The plates are shaken at intervals to effect mixing of reactants, and the acylation is allowed to proceed at room temperature overnight. Removal of the solvents in a stream of air or under vacuum then affords the compounds listed in TABLE 1.

All the amines and acid chlorides used above are either commercially available or can be easily prepared by one having ordinary skill in the organic chemistry art utilizing well known procedures.

In TABLE 1, "MS" refers to mass spectral data, "% inhib" refers to percentage of inhibition at 25 μM concentration in CMV polymerase assay.

                                      TABLE 1                                      __________________________________________________________________________                                     MS % Inhib                                     __________________________________________________________________________     1  (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-                                                          520                                                                               100.2                                          thiadiazol-2-yl)-9-octadecenamide                                             2 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol- -- 100.1                                              2-yl)-1,3-dioxo-1,3-dihydro-2-benzofu                                        ran-5-carboxamide                             3 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3- 419 100.0                                            dioxo-1,3-dihydro-2-benzofuran-5-carb                                        oxamide                                       4 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3- 443 100.0                                             dihydro-2-benzofuran-5-carboxamide                                            5 (E)-N-(5-{[2-(1-methyl-2-pyrrolidiny                                        l)ethyl]amino}-1,3,4- 492 99.9                                                   thiadiazol-2-yl)-9-octadecenamide                                             6 N-{5-[(2-anilinoethyl)amino]-1,3,4-t                                        hiadiazol-2-yl}-1,3- 410 99.9                  dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,                                 7 N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1,3- 399 99.8                                               dioxo-1,3-dihydro-2-benzofuran-5-carb                                        oxamide                                       8 N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}- 431 99.8                                                 1,3-dioxo-1,3-dihydro-2-benzofuran-5-                                        carboxamide                                   9 1,3-dioxo-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 401 99.8                    thiadiazol-2-yl)-1,3-dihydro-2-benzofuran-5-                                   carboxamide                                                                   10 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2- 434 99.7                                              yl)-1,3-dioxo-1,3-dihydro-2-benzofura                                        n-5-carboxamide                               11 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 421 99.6                                             yl}-1,3-dihydro-2-benzofuran-5-carbox                                        amide                                         12 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}- 449 99.5                                              1,3-dioxo-1,3-dihydro-2-benzofuran-5-                                        carboxamide                                   13 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2- 483 99.3                                                  yl}-1,3-dioxo-1,3-dihydro-2-benzofura                                        n-5-carboxamide                               14 (E)-N-(5-{[3-(4-methylpiperazino)propyl]amino}-1,3,4- 521 99.0                                                 thiadiazol-2-yl)-9-octadecenamide                                             15 N-(5-{[4-(aminosulfonyl)phenethyl]a                                        mino}-1,3,4-thiadiazol- 474 98.8                                                 2-yl)-1,3-dioxo-1,3-dihydro-2-benzofu                                        ran-5-carboxamide                             16 N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}- 441 98.7                                             1,3-dioxo-1,3-dihydro-2-benzofuran-5-                                        carboxamide                                   17 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}- 471 98.6                                               1,3-dioxo-1,3-dihydro-2-benzofuran-5-                                        carboxamide                                   18 (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- -- 98.3                     thiadiazol-2-yl)-9-octadecenamide                                             19 (E)-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4- 478 97.7                    thiadiazol-2-yl)-9-octadecenamide                                             20 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 425 97.7                     thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-                                      benzofuran-5-carboxamide                                                      21 1,3-dioxo-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 421 97.4                                              1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-                                        benzofuran-5-                                  carboxamide                                                                   22 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 387 97.2                                             amino)-1,3,4-thiadiazol-2-yl]-2-metho                                        xybenzamide                                   23 (E)-N-(5-{[2-(dimethylamino)ethyl]amino}-1,3,4-thiadiazol- 452 97.0                                            2-yl)-9-octadecenamide                      24 1,3-dioxo-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]- 395 95.6                                               1,3-dihydro-2-benzofuran-5-carboxamid                                        e                                             25 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 425 93.9                                             amino)-1,3,4-thiadiazol-2-yl]-1,3-dio                                        xo-1,3-dihydro-2-                              benzofuran-5-carboxamide                                                      26 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol- 484 93.1                                               2-yl)-2-ethoxy-1-naphthamide                                                  27 N-(5-{[3-(cyclohexylamino)propyl]am                                        ino}-1,3,4- 454 92.9                           thiadiazol-2-yl)-2-ethoxy-1-naphthamide                                       28 (E)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]- 421 92.6                                                   9-octadecenamide                            29 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo- 387 92.4                                             1,3-dihydro-2-benzofuran-5-carboxamid                                        e                                             30 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol- 458 91.8                                               2-yl)-2,6-dichlorobenzamide                 31 (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-9- 477 91.8                                                 octadecenamide                              32 (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 416 90.6                    thiadiazol-2-yl)-3-phenyl-2-propenamide                                       33 1,3-dioxo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4- 425 90.1                                                thiadiazol-2-yl)-1,3-dihydro-2-benzof                                        uran-5-carboxamide                            34 (E)-3-(2-chlorophenyl)-N-{5-[(cyclopropylmethyl)amino]- 335 89.9                                               1,3,4-thiadiazol-2-yl}-2-propenamide        35 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2- 516 89.7                                             yl)-2,4,6-triisopropylbenzamide                                               36 N-(5-{[3-(cyclohexylamino)propyl]am                                        ino}-1,3,4-thiadiazol- 486 87.6                                                  2-yl)-2,4,6-triisopropylbenzamide                                             37 2,6-dichloro-N-(5-{[3-(cyclohexylam                                        ino)propyl]amino}- 428 87.4                    1,3,4-thiadiazol-2-yl)benzamide                                               38 (E)-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}- 561 87.3         9-octadecenamide                                                              39 1,3-dioxo-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol- 387 87.1                                             2-yl}-1,3-dihydro-2-benzofuran-5-carb                                        oxamide                                       40 N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2- 407 86.3                                             yl]-1,3-dioxo-1,3-dihydro-2-benzofura                                        n-5-carboxamide                               41 (E)-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2- 491 85.7                                              yl)-9-octadecenamide                        42 (E)-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}- 477 84.6                                             9-octadecenamide                            43 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol- 449 83.9                                            2-yl}-2-ethoxy-1-naphthamide                                                  44 N-{5-[(1-naphthylmethyl)amino]-1,3,                                        4-thiadiazol-2-yl}- 396 83.3                   5-nitro-2-furamide                                                            45 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}- 488                                             83.1                                           2-ethoxy-1-naphthamide                                                        46 4-cyano-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol- 440 82.3                                            2-yl}benzamide                              47 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2- 399 81.6                                              yl)-5-nitro-2-furamide                      48 (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}- 489 81.5                                              9-octadecenamide                            49 4-({[5-(undecylamino)-1,3,4-thiadiazol-2-yl]amino}- -- 80.3                  carbonyl)benzenesulfonyl fluoride                                             50 (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 430 79.8                                                   thiadiazol-2-yl)-3-phenyl-2-propenami                                        de                                            51 (E)-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-9- 535 79.5                   octadecenamide                                                                52 N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1- -- 78.7                                                  benzothiophen-2-carboxamide                 53 (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 515 77.9                                                   thiadiazol-2-yl}-9-octadecenamide                                             54 1,3-dioxo-N-{5-[(4-pyridinylmethyl)                                        amino]-1,3,4- 382 77.7                         thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide                       55 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}- 495 77.6                                               2-ethoxy-1-naphthamide                      56 2,6-dichloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4- 469 77.4                                                   thiadiazol-2-yl}benzamide                   57 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 516 76.3                        thiadiazol-2-yl)-4-iodobenzamide                                              58 (E)-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4- 517 75.8                    thiadiazol-2-yl)-9-octadecenamide                                             59 4-iodo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol- 479 74.6                                                  2-yl}benzamide                              60 5-nitro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]- -- 74.5                  2-furamide                                                                    61 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol- 509 74.2                  2-yl}-2-ethoxy-1-naphthamide                                                  62 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 416 74.0                      thiadiazol-2-yl)-1-benzothiophene-2-carboxamide                               63 2,6-dichloro-N-{5-[(3,3-diphenylpropyl)amino] 483 73.8                       1,3,4-thiadiazol-2-yl}benzamide                                               64 (E)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4- 575 73.6                         thiadiazol-2-yl}-9-octadecenamide                                             65 4-cyano-N-[5-(undecylamino)-1,3,4-thiadiazol- 400 72.2                       2-yl]benzamide                                                                66 2-ethoxy-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 406 71.9                     thiadiazol-2-yl}-1-naphthamide                                                67 (E)-3-(2-chlorophenyl)-N-{5-[(4-fluorobenzyl)amino]- 389 71.7                                                  1,3,4-thiadiazol-2-yl}-2-propenamide        68 N-(5-{[4-(aminosulfonyl)phenthyl]amino}-1,3,4- 530 71.1                      thiadiazol-2-yl)-4-iodobenzamide                                              69 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}- 434 70.6                                                  2-ethoxy-1-naphthamide                      70 2-ethoxy-N-{5-[(2-pyridinylmethyl)amino]-1,3,4- 406 70.4                     thiadiazol-2-yl}-1-naphthamide                                                71 2-ethoxy-N-{5-[(4-fluorobenzyl)amino]-1,3,4- 423 69.8                        thiadiazol-2-yl}-1-naphthamide                                                72 (E)-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 470 69.3                          thiadiazol-2-yl}-9-octadecenamide                                             73 2,6-dichloro-N-{5-[(3,4-dichlorobenzyl)amino]- 449 69.1                      1,3,4-thiadiazol-2-yl}benzamide                                               74 4-cyano-N-{5-[(4-fluorobenzyl)amino]-1,3,4- 354 69.0                         thiadiazol-2-yl}benzamide                                                     75 (E)-3-(2-chlorophenyl)-N-(5-{[3-(cyclohexylamino)- 420 68.8                  propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide                            76 2,6-dichloro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenyl- 419 68.5                                                 amino)-1,3,4-thiadiazol-2-yl]benzamid                                        e                                             77 (E)-3-phenyl-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 357 68.3                                                  thiadiazol-2-yl)-2-propenamide                                                78 2-ethoxy-N-{5-[(2-thienylmethyl)ami                                        no]-1,3,4-thiadiazol- 411 68.2                                                   2-yl}-1-naphthamide                         79 tert-butyl-3-({5-[(E)-9-octadecenoylamino]-1,3,4- -- 68.0                    thiadiazol-2-yl}amino)propanoate                                              80 3-nitro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]- -- 67.9                  benzamide                                                                     81 (E)-3-phenyl-N-{5-[(4-phenylbutyl)amino]-1,3,4- 379 67.9                     thiadiazol-2-yl}-2-propenamide                                                82 4-cyano-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}- 389 67.7                       1,3,4-thiadiazol-2-yl)benzamide                                               83 4-cyano-N-{5-[(2,2-diphenylethyl)amino]-1,3,4- 426 67.7                      thiadiazol-2-yl}benzamide                                                     84 2,6-dichloro-N-{5-[(4-pyridinylmethyl)amino]- 380 67.6                       1,3,4-thiadiazol-2-yl}benzamide                                               85 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4- 464 67.3                         thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-                           5-carboxamide                                                                 86 ethyl 4-[(5-{[(2-ethoxy-1-naphthyl)carbonyl]amino}- 470 67.0                                                   1,3,4-thiadiazol-2-yl)amino]tetrahydr                                        o-1(2H)-                                       pyridinecarboxylate                                                           87 N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 455 67.0                     thiadiazol-2-yl)-2,4,6-triisopropylbenzamide                                  88 (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 450 66.5                    thiadiazol-2-yl)-3-(2-chlorophenyl)-2-propenamide                             89 2-ethoxy-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}- 409 66.3                   1,3,4-thiadiazol-2-yl)-1-naphthamide                                          90 4-{[(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 446 66.1                       thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride                       91 ethyl 4-({5-[(E)-9-octadecenoylamino]-1,3,4-thiadiazol- 272 66.1                                               2-yl}amino)tetrahydro-1(2H)-pyridinec                                        arboxylate                                    92 2,6-dichloro-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 399 66.1                                                  thiadiazol-2-yl)benzamide                   93 2-ethoxy-N-[5-(1,2,3,4-tetrahydro-1-naphthaienylamino)- 445 66.0                                               1,3,4-thiadiazol-2-yl]-1-naphthamide        94 (E)-3-phenyl-N-{5-[(4-pyridinylmethyl)amino]-1,3,4- 338 65.9                                                   thiadiazol-2-yl}-2-propenamide                                                95 N-[5-(2,3-dihydro-1H-inden-1-ylamin                                        o)-1,3,4-thiadiazol- 431 65.9                  2-yl]-2-ethoxy-1-naphthamide                                                  96 N-{5-[(1,3-benzodioxol-5-ylethyl)amino]-1,3,4-thiadiazol- 423 65.9                                             2-yl}-2,6-dichlorobenzamide                 97 2-ethoxy-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 425 65.8                    thiadiazol-2-yl)-1-naphthamide                                                98 (E)-3-(2-chlorophenyl)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]- 375 65.7                                             amino}-1,3,4-thiadiazol-2-yl)-2-prope                                        namide                                        99 2,6-dichloro-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}- 397 65.6                                                1,3,4-thiadiazol-2-yl)benzamide                                               100 (E)-N-{5-[(3,4-dimethoxybenzyl)ami                                        no]-1,3,4-thiadiazol- -- 65.1                  2-yl}-9-octadecenamide                                                        101 2,6-dichloro-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 429 65.0                                                   thiadiazol-2-yl}benzamide                   102 4-cyano-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 356 64.9                    thiadiazol-2-yl)benzamide                                                     103 4-cyano-N-[5-(cycloheptylamino)-1,3,4-thiadiazol- 342 64.9                  2-yl]benzamide                                                                104 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-5- 352 64.7                  nitro-2-furamide                                                              105 (E)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]- 485 64.6                  9-octadecenamide,                                                             106 5-chloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 389 64.2                   yl]pentanamide,                                                               107 (E)-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 511 63.8                                                   1,3,4-thiadiazol-2-yl]-9-octadecenami                                        de                                            108 (E)-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}- 513 63.5                                              9-octadecenamide                            109 2,4,6-triisopropyl-N-(5-{[2-(1-methyl-2-pyrrolidinyl)ethyl] 458                                             63.4                                           amino]-1,3,4-thiadiazol-2-yl)benzamide                                        110 (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol- 454 62.9         2-yl}-3-(2-chlorophenyl)-2-propenamide                                        111 4-[({5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- 483 62.6                                                yl}amino)carbonyl]benzenesulfonyl                                            fluoride                                      112 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 428 62.5                     thiadiazol-2-yl)-4-(trifluoromethyl)benzamide                                 113 (E)-N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol- 435 62.2                                                2-yl}-9-octadecenamide                      114 (E)-3-phenyl-N-(5-{[2-(phenylsulfanyl)ethyl]amino}- 383 62.1                                                  1,3,4-thiadiazol-2-yl)-2-propenamide        115 2,6-dichloro-N-[5-(2,3-dihydro-1H-inden-1-ylamino)- 405 62.0                                                  1,3,4-thiadiazol-2-yl]benzamide                                               116 N-{5-[(2-ethylhexyl)amino]-1,3,4-t                                        hiadiazol-2-yl}- 401 61.9                      1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide                              117 (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]- 415 61.5                      1,3,4-thiadiazol-2-yl}-3-(2-chlorophenyl)-2-propenamide                       118 2,6-dichloro-N-{5-[(2-thienylmetyl)amino]-1,3,4- 385 61.2                   thiadiazol-2-yl}benzamide                                                     119 (E)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol- 521 60.6                                                 2-yl}-9-octadecenamide                      120 tert-butyl 3-[(5-{[(E)-3-phenyl-2-propenoyl]amino}- 375 60.0                                                  1,3,4-thiadiazol-2-yl)amino]propanoat                                        e                                             121 2,4-difluoro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 411 60.0                                                 yl]benzamide                                122 N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol- 465 59.5                                                  2-yl}-2-ethoxy-1-naphthamide                                                  123 (E)-N-(5-{[2-(acetylamino)ethyl]am                                        ino}-1,3,4- 466 59.2                           thiadiazol-2-yl)-9-octadecenamide                                             124 (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}- 386 59.2                       1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide                                 125 (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 464 58.9                                                  thiadizol-2-yl)-3-(2-chlorophenyl)-2-                                        propenamide                                   126 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 395 58.9                     thiadiazol-2-yl)-5-nitro-2-furamide                                           127 4-cyano-N-(5-{[3-(cyclohexylamino)propyl]amino- 385 58.5                    1,3,4-thiadiazol-2-yl)benzamide                                               128 N-(5-{[4-(aminosulfonyl)phenethyl]amino}1,3,4- 530 58.3                     thiadiazol-2-yl)-2,4,6-triisopropylbenzamide                                  129 (E)-N-(5-{[2-(ethylsulfanyl)ethyl]amino}1,3,4- 469 58.3                     thiadiazol-2-yl)-9-octadecenamide                                             130 (E)-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 372 58.2                  1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide                                 131 5-nitro-N-{5-[(4-phenylbutyl)amino]-1,3,4- 388 58.0                         thiadiazol-2-yl}-2-furamide                                                   132 ethyl 4-({5-[(2,6-dichlorobenzoyl)amino]-1,3,4- 444 57.0                    thiadiazol-2-yl}amino)tetrahydro-1(2H)-                                        pyridinecarboxylate                                                           133 (E)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}- 355 57.0                      1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide                                 134 N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4- 497 56.9                           thiadiazol-2-yl}-4-iodobenzamide                                              135 3-nitro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]- 391 56.6                    amino}-1,3,4-thiadiazol-2-yl)benzamide                                        136 2-ethoxy-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 455 56.5                     thiadiazol-2-yl}-1-naphthamide                                                137 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 405 56.4                     thiadiazol-2-yl)-3-nitrobenzamide                                             138 N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}- 421 56.2                                                  4-(trifluoromethyl)benzamide                                                  139 (E)-3-phenyl-N-{5-[(2-pyridinylmet                                        hyl)amino]- 338 56.2                           1,3,4-thiadiazol-2-yl}-2-propenamide                                          140 4-cyano-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4- 404 56.2                    thiadiazol-2-yl}benzamide                                                     141 2-ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}- 458 55.7                     1,3,4-thiadiazol-2-yl)-1-naphthamide                                          142 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 472 55.4                    thiadiazol-2-yl)-3,4-dichlorobenzamide                                        143 4-cyano-N-{5-[(4-phenylbutyl)amino]-1,3,4- 378 55.4                         thiadiazol-2-yl}benzamide                                                     144 2,6-dichloro-N-{5-[(4-fluorobenzyl)amino]-1,3,4- 397 55.2                   thiadiazol-2-yl}benzamide                                                     145 2-ethoxy-N-[5-(undecylamino)-1,3,4-thiadiazol- 469 54.9                     2-yl]-1-naphthamide                                                           146 2,6-dichloro-N-{5-[(2-cyanoethyl)amino]-1,3,4- 342 54.8                     thiadiazol-2-yl}benzamide                                                     147 4-iodo-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 501 54.7                     yl]benzamide                                                                  148 N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4- 435 54.6                        thiadiazol-2-yl)-4-iodobenzamide                                              149 (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 524 54.5                    thiadiazol-2-yl)-9-octadecenamide                                             150 N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 402 54.5                      1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide                         151 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol- 462 54.0                                               2-yl}-2,6-dichlorobenzamide                 152 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 484 53.9                    thiadiazol-2-yl)-4-bromobenzamide                                             153 (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 390 53.7                    thiadiazol-2-yl)-3-phenyl-2-propenamide                                       154 (E)-3-(2-chlorophenyl)-N-{5-[(2,2-diphenylethyl)amino]- -- 53.6                                               1,3,4-thiadiazol-2-yl}-2-propenamide        155 4-cyano-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2- 386 53.3         yl}benzamide                                                                  156 2,6-dichloro-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 380 53.2                                                  thiadiazol-2-yl}benzamide                   157 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1- 411 53.0         naphthamide                                                                   158 4-cyano-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 371 52.9                                                1,3,4-thiadiazol-2-yl)benzamide                                               159 4-bromo-N-(5-{[3-(cyclohexylamino)                                        propyl]amino}-1,3,4- 440 52.8                  thiadiazol-2-yl)benzamide                                                     160 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 396 52.6                     thiadiazol-2-yl)-2,4-difluorobenzamide                                        161 (E)-3-(2-chlorophenyl)-N-{5-[(2-pyridinylmethyl)amino]- 372 51.9                                              1,3,4-thiadiazol-2-yl}-2-propenamide        162 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2- 374                                             51.8                                           yl)-4-methylbenzamide                                                         163 4-bromo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4- 437 51.5                                                 thiadiazol-2-yl)benzamide                   164 (E)-3-(2-chlorophenyl)-N-{5-[(2-thienylmethyl)amino]-1,3,4- 377                                             51.4                                           thiadiazol-2-yl}-2-propenamide                                                165 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2- 369                                            51.3                                           yl}-5-chloropentanamide                                                       166 (E)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 517                                           51.1                                           amino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide                                167 4-methyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 389 50.8                   yl]benzamide                                                                  168 3,4-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 421                                            50.8                                           yl}benzamide                                                                  169 2,4,6-triisopropyl-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4- 444                                         50.7                                           thiadiazol-2-yl)benzamide                                                     170 4-bromo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 433 50.5                                              yl}benzamide                                171 (E)-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9- 472                                           49.9                                           octadecenamide                                                                172 3,4-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 428                                             49.7                                           thiadiazol-2-yl)benzamide                                                     173 2,4,6-triisopropyl-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 487 49.5                                             thiadiazol-2-yl}benzamide                   174 2,6-dichloro-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2- 369                                            49.5                                           yl}benzamide                                                                  175 3,5-difluoro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 411 49.4                                                 yl]benzamide                                176 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 527                                           49.4                                           triisopropylbenzamide                                                         177 N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2- 369 49.0                                                  yl}-2-ethoxy-1-naphthamide                  178 (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 381 49.0                                                  thiadiazol-2-yl}-3-phenyl-2-propenami                                        de                                            179 (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2- 500 48.5                                                 yl}-9-octadecenamide                        180 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- -- 48.4                     thiadiazol-2-yl}-1-benzothiophene-2-carboxamide                               181 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]1,3,4- 369 48.3                     thiadiazol-2-yl}-4-methylbenzamide                                            182 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- 437 48.2                                                  yl}-2,4-difluorobenzamide                   183 5-chloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4- 429 48.1                   thiadiazol-2-yl}pentanamide                                                   184 1,3-dioxo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 434 47.8                                              1,3,4-thiadiazol-2-yl)-1,3-dihydro-2-                                        benzofuran-5-carboxamide                      185 (E)-3-(2-chlorophenyl)-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 391                                          47.6                                           thiadiazol-2-yl)-2-propenamide                                                186 5-chloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- 415                                            47.4                                           yl}pentanamide                                                                187 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1- -- 47.2                                             benzothiophene-2-carboxamide                                                  188 N-{5-[(2,2-diphenylethyl)amino]-1,                                        3,4-thiadiazol-2- 437 47.2                     yl}-3,5-difluorobenzamide                                                     189 4-{[(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 442 47.1                   thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride                       190 N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2- 406 47.1                                                   yl}-3-nitrobenzamide                        191 3,4-dichloro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]- 414 47.1                                                 amino}-1,3,4-thiadiazol-2-yl)benzamid                                        e                                             192 5-nitro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 386 47.0                                               1,3,4-thiadiazol-2-yl]-2-furamide                                             193 (E)-3-(2-chlorophenyl)-N-(5-{[2-(e                                        thylsulfanyl)ethyl] 369 46.9                   amino}-1,3,4-thiadiazol-2-yl)-2-propenamide                                   194 4-bromo-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 455 46.8                    yl]benzamide                                                                  195 4-[({5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2- 443 46.7                                                 yl}amino)carbonyl]benzenesulfonyl                                            fluoride                                      196 (E)-3-(2-chlorophenyl)-N-[5-(cycloheptylamino) 1,3,4- 377 46.2                                                thiadiazol-2-yl]-2-propenamide                                                197 2,4-difluoro-N-{5-[(4-phenylbutyl)                                        amino]-1,3,4- 389 46.2                         thiadiazol-2-yl}benzamide                                                     198 4-iodo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4- -- 46.0                                                   thiadiazol-2-yl)benzamide                   199 (E)-N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-9- 435 46.0                                                 octadecenamide                              200 5-chloro-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 375 45.3                     thiadiazol-2-yl}pentanamide                                                   201 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2- 362 45.3                        yl]-3-nitrobenzamide                                                          202 3,4-dichloro-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}- 397 45.0                                               1,3,4-thiadiazol-2-yl)benzamide                                               203 4-iodo-N-(5-{[3-(2-oxo-1-pyrrolidi                                        nyl)propyl]amino}- 472 45.0                    1,3,4-thiadiazol-2-yl)benzamide                                               204 4-[({5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2- 422 45.0                                                   yl}amino)carbonyl]benzenesulfonyl                                            fluoride                                      205 2,4-difluoro-N-(5-{[2-(phenylsulfanyl)ethyl]amino}- 393 44.9                                                  1,3,4-thiadiazol-2-yl)benzamide                                               206 2-ethoxy-N-(5-{[2-(phenylsulfanyl)                                        ethyl]amino}-1,3,4- 451 44.9                   thiadiazol-2-yl)-1-naphthamide                                                207 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2- 473 44.7         ethoxy-1-naphthamide                                                          208 (E)-3-(2-chlorophenyl)-N-(5-{[3-(2-oxo-1-pyrrolidinyl)- 406 44.7                                              propyl]amino}-1,3,4-thiadiazol-2-yl)-                                        2-propenamide                                 209 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 392 44.7                                            amino)-1,3,4-thiadiazol-2-yl]-5-nitro                                        -2-furamide                                   210 (E)-3-(2-chlorophenyl)-N-[5-(phenethylamino)-1,3,4- 385 44.6                                                  thiadiazol-2-yl]-2-propenamide                                                211 (E)-N-(5-{[2-(ethylsulfanyl)ethyl]                                        amino}-1,3,4-thiadiazol- 335 44.3                                                2-yl)-3-phenyl-2-propenamide                                                  212 N-(5-{[3-(cyclohexylamino)propyl]a                                        mino}-1,3,4-thiadiazol- 486 44.2                                                 2-yl)-4-iodobenzamide                       213 2-ethoxy-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2- 395 44.2                                             yl}-1-naphthamide                           214 N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1- -- 44.1                                              benzothiophene-2-carboxamide                                                  215 (E)-N-(5-{[2-(1H-imidazol-4-yl)eth                                        yl]amino}-1,3,4-thiadiazol- 341 44.1                                             2-yl)-3-phenyl-2-propenamide                                                  216 (E)-3-(2-chlorophenyl)-N-[5-(undec                                        ylamino)-1,3,4-thiadiazol- -- 43.9                                               2-yl]-2-propenamide                         217 4-[({5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2- 497 43.9                                               yl}amino)carbonyl]benzenesulfonyl                                            fluoride                                      218 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4- 450 43.6                        thiadiazol-2-yl}-1-benzothiophene-2-carboxamide                               219 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)- 490                                            43.6                                           2,4,6-triisopropylbenzamide                                                   220 (E)-N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}- 360                                             43.6                                           3-phenyl-2-propenamide                                                        221 (E)-3-(2-chlorophenyl)-N-(5-{[3-(1H-imidazol-1-yl)propyl] 389 43.5                                            amino}-1,3,4-thiadiazol-2-yl)-2-prope                                        namide                                        222 N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 368 43.2                                            benzothiophene-2-carboxamide                                                  223 N-(5-{[4-(aminosulfonyl)benzyl]ami                                        no}-1,3,4-thiadiazol-2- 446 43.1                                                 yl)-1-benzothiophene-2-carboxamide                                            224 N-{5-[(2,2-diphenylethyl)amino]-1,                                        3,4-thiadiazol-2-yl}-2- 431 43.0                                                 methoxybenzamide                            225 2,6-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol- 421 42.9         2-yl}benzamide                                                                226 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}- 460 42.9                                             3-nitrobenzamide                            227 N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1- 355 42.8         naphthamide                                                                   228 3,5-difluoro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 382 42.8         1,3,4-thiadiazol-2-yl)benzamide                                               229  271 42.5                                                                  230 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol- 418 42.3         2-yl)-4-methylbenzamide                                                       231 2-ethoxy-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}- 447                                            42.3                                           1-naphthamide                                                                 232 2,4,6-triisopropyl-N-{5-[(2-piperidinoethyl)amino]-1,3,4- 458 42.2                                            thiadiazol-2-yl}benzamide                   233 2-ethoxy-N-[5-(neopentylamino)-1,3,4-thiadiazol-2-yl]- 385 42.1                                               1-naphthamide                               234 N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1- 387 42.0         benzothiophene-2-carboxamide                                                  235  257 41.8                                                                  236 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 396 41.6                                               benzothiophene-2-carboxamide                                                  237 N-{5-[(2-thienylmethyl)amino]-1,3,                                        4-thiadiazol-2-yl}-1- 373 41.5                                                   benzothiophene-2-carboxamide                                                  238 (E)-N-{5-[(2-furylmethyl)amino]-1,                                        3,4-thiadiazol-2-yl}-9- 461 41.5                                                 octadecenamide                              239 4-(trifluoromethyl)-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 443                                             41.4                                           yl]benzamide                                                                  240 (E)-3-(2-chlorophenyl)-N-{5-[(3,3-diphenylpropyl)amino]- -- 41.3                                              1,3,4-thiadiazol-2-yl}-2-propenamide        241 2,6-dichloro-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol- 380                                          41.3                                           2-yl}benzamide                                                                242 2-ethoxy-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 423 41.3                                             thiadiazol-2-yl)-1-naphthamide                                                243 N-{5-[(3,3-diphenylpropyl)amino]-1                                        ,3,4-thiadiazol-2-yl}- 451 41.1                                                  2,4-difluorobenzamide                       244 4-cyano-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol- 396                                             41.0                                           2-yl}benzamide                                                                245 4-[({5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 435 41.0                  yl}amino)carbonyl]benzenesulfonyl fluoride                                    246 (E)-N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4- 465 40.9                                                  thiadiazol-2-yl}-9-octadecenamide                                             247 3,4-dichloro-N-{5-[(2-furylmethyl)                                        amino]-1,3,4-thiadiazol-2- 369 40.9                                              yl}benzamide                                248 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 466 40.8         triisopropylbenzamide                                                         249 (E)-N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}- 432 40.6                                               9-octadecenamide                            250 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2,4,6- 443 40.5                                                triisopropylbenzamide                       251 (E)-3-(2-chlorophenyl)-N-{5-[(2-furylmethyl)amino]-1,3,4- 361 40.3                                            thiadiazol-2-yl}-2-propenamide                                                252 N-(5-{[2-(1H-indol-3-yl)ethyl]amin                                        o}-1,3,4-thiadiazol-2-yl)- 490 40.2                                              4-iodobenzamide                             253 (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- 554                                            40.1                                           yl}-9-octadecenamide                                                          254 5-chloro-N-(5-{[2-(phenylsulfanyl)ethyl]amino]-1,3,4- 371 40.0                                                thiadiazol-2-yl)pentanamide                 255 2,6-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 432 39.9                                             thiadiazol-2-yl)benzamide                   256 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-                                            373 39.8                                       2-carboxamide                                                                 257 N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene- --                                             39.8                                           2-carboxamide                                                                 258 N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)- 376 39.7         1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide                              259 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2- 472                                            39.6                                           yl)-2,6-dichlorobenzamide                                                     260 2,4,6-triisopropyl-N-{5-[(4-phenylbutyl)amino]-1,3,4- 479 39.6                                                thiadiazol-2-yl}benzamide                   261 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)- 451                                         39.5                                           1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide                                 262 (E)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-3- 351 39.5                                                  phenyl-2-propenamide                        263 3,4-chloro-N-{5-[(4-pyridinylmethyl)amino]-1,3,4- 380 39.4                  thiadiazol-2-yl}benzamide                                                     264 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-5- 375 39.2                                               nitro-2-furamide                            265 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol- 520 39.1                                               2-yl}-2,4,6-triisopropylbenzamide                                             266 2,4,6-triisopropyl-N-{5-[(4-pyridi                                        nylmethyl)amino]-1,3,4- 438 38.8                                                 thiadiazol-2-yl}benzamide                   267 N-(5-{[4-(aminosulfonyl)phenethyl]amino}- 460 38.7                          1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide                         268 (E)-3-(2-chlorophenyl)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}- --                                             38.7                                           1,3,4-thiadiazol-2-yl)-2-propenamide                                          269 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1- --                                           38.5                                           benzothiophene-2-carboxamide                                                  270 2-ethoxy-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-1- 419 38.4                                             naphthamide                                 271 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)- 409                                            38.4                                           3-nitrobenzamide                                                              272 4-bromo-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 409 38.2                                              thiadiazol-2-yl)benzamide                   273 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol- 435 38.1         2-yl}-4-bromobenzamide                                                        274 (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-3- 343 38.1                                                phenyl-2-propenamide                        275 N-(5-{[3-(cyclohexylamino)propyl]amino]-1,3,4-thiadiazol-2- 396                                             37.9                                           yl)-3,5-difluorobenzamide                                                     276 (E)-3-(2-chlorophenyl)-N-[5-(cyclobutylamino)-1,3,4- 335 37.9                                                 thiadiazol-2-yl]-2-propenamide                                                277 N-{5-[(3,3-diphenylpropyl)amino]-1                                        ,3,4-thiadiazol-2- -- 37.9                     yl}-1-benzothiophene-2-carboxamide                                            278 4-({[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl] 399 37.5                   amino}carbonyl)benzenesulfonyl fluoride                                       279 (E)-N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4- 497 37.4                   thiadiazol-2-yl]-9-octadecenamide                                             280 2,6-dichloro-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4- 439 37.3                                                thiadiazol-2-yl}benzamide                   281 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}- 451 37.3                                             3,5-difluorobenzamide                       282 5-nitro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-2- 360 37.1                                              furamide                                    283 2,6-dichloro-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2- 401                                             37.0                                           yl}benzamide                                                                  284 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol- 432 36.7                                               2-yl)-4-(trifluoromethyl)benzamide                                            285 (E)-N-{5-[(cyclohexylmethyl)amino]                                        -1,3,4-thiadiazol-2-yl}-9- 477 36.7                                              octadecenamide                              286 (E)-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}-9- 493 36.3                                             octadecenamide                              287 N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-1- 317 36.2                  benzothiophene-2-carboxamide                                                  288 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2- 443 36.2                        yl]-4-iodobenzamide                                                           289 4-iodo-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol- 438 36.0                                             2-yl}benzamide                              290 (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol- 420 35.9         2-yl}-3-phenyl-2-propenamide                                                  291 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3- 385 35.7                                               nitrobenzamide                              292 2,6-dichloro-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4- 377 35.6                                             thiadiazol-2-yl)benzamide                   293 tert-butyl 3-[(5-{[(2-ethoxy-1-naphthyl)carbonyl]amino}- 443 35.5                                             1,3,4-thiadiazol-2-yl)amino]propanoat                                        e                                             294 (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}- 400 35.4                                             3-(2-chlorophenyl)-2-propenamide                                              295 3,4-dichloro-N-(5-{[2-(1H-indol-3-                                        yl)ethyl]amino}-1,3,4- -- 35.4                                                   thiadiazol-2-yl)benzamide                   296 5-nitro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4- 381                                             35.1                                           thiadiazol-2-yl)-2-furamide                                                   297 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}- -- 35.0                                              4-iodobenzamide                             298 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}- 450 35.0                                             5-nitro-2-furamide                          299 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2- 541 34.9                                                 yl}-2,4,6-triisopropylbenzamide                                               300 N-[5-(cycloheptylamino)-1,3,4-thia                                        diazol-2-yl]-3,5- 353 34.9                     difluorobenzamide                                                             301 N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 368 34.8                                            benzothiophene-2-carboxamide                                                  302 N-{5-[(4-fluorobenzyl)amino]-1,3,4                                        -thiadiazol-2-yl}-3- 374 34.8                  nitrobenzamide                                                                303 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2- 394                                          34.7                                           methoxybenzamide                                                              304 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2- 347 34.6                                             methoxybenzamide                            305 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 391 34.5                    thiadiazol-2-yl}-2,4-difluorobenzamide                                        306 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- 436 34.4                                                  yl}-5-nitro-2-furamide                      307 4-cyano-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2- 382 34.2                                               yl]methyl}amino)-1,3,4-thiadiazol-2-y                                        l]benzamide                                   308 2,4-dichloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 393 34.2                                               yl]benzamide                                309 4-bromo-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4- 389 34.0                                                  thiadiazol-2-yl)benzamide                   310 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2- 347 34.0                  methoxybenzamide                                                              311 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 458 33.9                       thiadiazol-2-yl)-3,4-dichlorobenzamide                                        312 5-chloro-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2- 371 33.9                                              yl]methyl}amino)-1,3,4-thiadiazol-2-y                                        l]pentanamide                                 313 (E)-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2- 539 33.9                                             yl}-9-octadecenamide                        314 N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1- 369 33.8                                            naphthamide                                 315 5-chloro-N-{5-[(cyclohexylmethyl)amino]-1,3,4- 331 33.8                     thiadiazol-2-yl}pentanamide                                                   316 5-chloro-N-[5-(cycloheptylamino)-1,3,4- 331 33.6                            thiadiazol-2-yl]pentanamide                                                   317 N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4- 411 33.6                     thiadiazol-2-yl)-2,4,6-triisopropylbenzamide                                  318 2-ethoxy-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4- 403 33.6                                                 thiadiazol-2-yl)-1-naphthamide                                                319 (E)-3-(2-chlorophenyl)-N-[5-(neope                                        ntylamino)-1,3,4- 351 33.5                     thiadiazol-2-yl]-2-propenamide                                                320 (E)-3-(2-chlorophenyl)-N-[5-({[(2R)-6,6-dimethylbicyclo -- 33.5                                               [3.1.1]hept-2-yl]methyl}amino)-1,3,4-                                        thiadiazol-2-yl]-2-                            propenamide                                                                   321 5-chloro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2- 343 33.2                                            yl}pentanamide                              322 (E)-3-(2-chlorophenyl)-N-(5-{[2-(phenylsulfanyl)ethyl]amino}- --                                            33.2                                           1,3,4-thiadiazol-2-yl)-2-propenamide                                          323 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-4- 331 33.0                  methylbenzamide                                                               324 N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 455 32.9                    thiadiazol-2-yl)-4-iodobenzamide                                              325 5-chloro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 360 32.8                                               1,3,4-thiadiazol-2-yl)pentanamide                                             326 (E)-N-{5-[(4-fluorobenzyl)amino]-1                                        ,3,4-thiadiazol-2-yl}-3- 355 32.7                                                phenyl-2-propenamide                        327 2-methoxy-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 355 32.5                                                  yl]benzamide                                328 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol- 498 32.4         2-yl)-2-ethoxy-1-naphthamide                                                  329 (E)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}- 387 32.4         3-phenyl-2-propenamide                                                        330 N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4- 371 32.2                     thiadiazol-2-yl-1-benzothiophene-2-carboxamide                                331 (E)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol- -- 32.1                                                2-yl}-3-phenyl-2-propenamide                                                  332 N-(5-{[2-(acetylamino)ethyl]amino}                                        -1,3,4-thiadiazol-2- 432 32.0                  yl)-2,4,6-triisopropylbenzamide                                               333 (E)-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2- 405 31.9                                             yl}-3-phenyl-2-propenamide                  334 2-methoxy-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 391 31.8                    thiadiazol-2-yl}benzamide                                                     335 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 429 31.7                    thiadiazol-2-yl)-4-cyanobenzamide                                             336 (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- -- 31.6                                                   thiadiazol-2-yl)-9-octadecenamide                                             337 3-nitro-N-(5-{[2-(2-thienyl)ethyl]                                        amino}-1,3,4- 376 31.6                         thiadiazol-2-yl)benzamide                                                     338 tert-butyl 3-({5-[(2,6-dichlorobenzoyl)amino]-1,3,4- 417 31.6                                                 thiadiazol-2-yl}amino)propanoate                                              339 N-{5-[(2-anilinoethyl)amino]-1,3,4                                        -thiadiazol-2-yl}-4- 466 31.5                  iodobenzamide                                                                 340 tert-butyl 3-[(5-{[(1,3-dioxo-1,3-dihydro-2-benzofuran-5- 419 31.5                                            yl)carbonyl]amino}-1,3,4-thiadiazol-2                                        -yl)amino]propanoate                          341 N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4- 427 31.3                                                iodobenzamide                               342 (E)-3-phenyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-2- 401 31.2         propenamide                                                                   343 N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4- 407 31.2                                                 thiadiazol-2-yl]-1-benzothiophene-2-c                                        arboxamide                                    344 ethyl 4-[(5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4- 436                                             31.1                                           1,3,4-thiadiazol-2-yl)amino]tetrahydro-1(2H)-                                  pyridinecarboxylate                                                           345 4-cyano-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 350 30.9                  yl]benzamide                                                                  346 5-chloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 378 30.7                                                 thiadiazol-2-yl)pentanamide                 347 3-nitro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4- 396                                            30.6                                           thiadiazol-2-yl]benzamide                                                     348 N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2- 359 30.4                                               methoxybenzamide                            349 N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 357 30.3                                                benzothiophene-2-carboxamide                                                  350 N-{5-[(3,4-dichlorobenzyl)amino]-1                                        ,3,4-thiadiazol-2- 414 30.3                    yl}-5-nitro-2-furamide                                                        351 4-bromo-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 444 30.3                                                  thiadiazol-2-yl)benzamide                   352 (E)-3-(2-chlorophenyl)-N-[5-[(4-pyridinylmethyl)amino]-1,3,4- 372                                           30.2                                           thiadiazol-2-yl}-2-propenamide                                                353 (E)-3-(2-chlorophenyl)-N-[5-(cyclopropylamino)-1,3,4- 321 30.2                                                thiadiazol-2-yl]-2-propenamide                                                354 5-chloro-N-[5-(phenethylamino)-1,3                                        ,4-thiadiazol-2-yl] 339 29.9                   pentanamide                                                                   355 N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2- 382 29.8                                            yl]-3-nitrobenzamide                        356 4-methyl-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 367 29.6                                             yl}benzamide                                357 (E)-3-(2-chlorophenyl)-N-{5-[(4-phenylbutyl)amino]-1,3,4- -- 29.4                                             thiadiazol-2-yl}-2-propenamide                                                358 N-{5-[(1,3-benzodioxol-5-ylmethyl)                                        amino]-1,3,4- 481 29.3                         thiadiazol-2-yl}-2,4,6-triisopropylbenzamide                                  359 4-methyl-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 339 29.1                                                   yl]benzamide                                360 (E)-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2- 343 29.0                                               yl}-3-phenyl-2-propenamide                  361 N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1- 385 28.8                                               benzothiophene-2-carboxamide                                                  362 3,5-difluoro-N-{5-[(1-naphthylmeth                                        yl)amino]-1,3,4- 397 28.8                      thiadiazol-2-yl}benzamide                                                     363 2,4-difluoro-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 397 28.8                                                   thiadiazol-2-yl}benzamide                   364 4-cyano-N-{5-[(cyclohexylmethyl)amino]-1,3,4- 342 28.7                      thiadiazol-2-yl}benzamide                                                     365 4-cyano-N-{5-[(2-thienylmethyl)amino]-1,3,4- 342 28.7                       thiadiazol-2-yl}benzamide                                                     366 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 434 28.6                    thiadiazol-2-yl)-2-methoxybenzamide                                           367 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4- 520 28.6                        thiadiazol-2-yl}-4-iodobenzamide                                              368 ethyl 4-({5-[(1-benzothiophen-2-ylcarbonyl)amino]- 432 28.5                                                   1,3,4-thiadiazol-2-yl}amino)tetrahydr                                        o-1(2H)-                                       pyridinecarboxylate                                                           369 2,6-dichloro-N-[5-(cycloheptylamino)-1,3,4- 385 28.3                        thiadiazol-2-yl]benzamide                                                     370 2,6-dichloro-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4- 386 28.3                                            thiadiazol-2-yl)benzamide                   371 4-{[(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4- 428 28.1                                                thiadiazol-2-yl)amino]carbonyl}benzen                                        esulfonyl fluoride                            372 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 391 28.1                    thiadiazol-2-yl}-3,5-difluorobenzamide                                        373 3,5-difluoro-N-{5-[(4-phenylbutyl)amino]-1,3,4- 389 28.1                    thiadiazol-2-yl}benzamide                                                     374 (E)-3-(2-chlorophenyl)-N-[5-(1,2,3,4-tetrahydro-1- 411 28.1                                                   naphthalenylamino)-1,3,4-thiadiazol-2                                        -yl]-2-propenamide                            375 3,4-dichloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 443 27.9                                                 yl]benzamide                                376 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-4- 483 27.9         (trifluoromethyl)benzamide                                                    377 2,6-dichloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 393 27.8                                               yl]benzamide                                378 (E)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 489 27.8                                                  thiadiazol-2-yl)-9-octadecenamide                                             379 (E)-N-{5-[(2-anilinoethyl)amino]-1                                        ,3,4-thiadiazol-2- 366 27.5                    yl}-3-phenyl-2-propenamide                                                    380 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2- 352 27.5                                                   yl}-5-nitro-2-furamide                      381 2,4,6-triisopropyl-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]- 472 27.4         amino}-1,3,4-thiadiazol-2-yl)benzamide                                        382 5-chloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 367 27.3                                             yl}pentanamide                              383 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2- 445 27.3                                                 yl}-2-methoxybenzamide                      384 3,4-dichloro-N-{5-[(cyclohexylmethyl)amino]-1,3,4- 385 27.2                                                   thiadiazol-2-yl}benzamide                   385 4-bromo-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- -- 27.2         yl}benzamide                                                                  386 4-bromo-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4- -- 26.9                     thiadiazol-2-yl}benzamide                                                     387 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 390 26.8                     thiadiazol-2-yl)-2-methoxybenzamide                                           388 tert-butyl 3-({5-[(2,4,6-triisopropylbenzoyl)amino]-1,3,4- 475 26.6         thiadiazol-2-yl}amino)propanoate                                              389 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 393 26.5                                            amino)-1,3,4-thiadiazol-2-yl]-3,5-dif                                        luorobenzamide                                390 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 418 26.3                    thiadiazol-2-yl)-5-chloropentanamide                                          391 (E)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4- 475 26.2                                                   thiadiazol-2-yl)-9-octadecenamide                                             392 2,6-dichloro-N-[5-(neopentylamino)                                        -1,3,4-thiadiazol-2- 359 26.2                  yl]benzamide                                                                  393 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-4- 354 26.1                                               methylbenzamide                             394 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2- 370 26.0                                               methoxybenzamide                            395 4-methyl-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 360 25.9                                               1,3,4-thiadiazol-2-yl)benzamide                                               396 2,4,6-triisopropyl-N-(5-{[2-(2-thi                                        enyl)ethyl]amino}-1,3,4- 457 25.9                                                thiadiazol-2-yl)benzamide                   397 (E)-3-(2-chlorophenyl)-N-(5-{[2-(1-pyrrolidinyl)ethyl]- 378 25.9                                              amino}-1,3,4-thiadiazol-2-yl)-2-prope                                        namide                                        398 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 458 25.9                       thiadiazol-2-yl)-4-(trifluoromethyl)benzamide                                 399 2,4,6-triisopropyl-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 438 25.8                                            thiadiazol-2-yl}benzamide                   400 (E)-N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2- 332 25.8         yl)-3-phenyl-2-propenamide                                                    401 N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 455 25.5         triisopropylbenzamide                                                         402 4-iodo-N-{5-[(1-naphthylmethyl)amino]-1,3,4- -- 25.5                        thiadiazol-2-yl}benzamide                                                     403 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- -- 25.3                                             amino)-1,3,4-thiadiazol-2-yl]-1-benzo                                        thiophene-2-carboxamide                       404 N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2- 372 25.2                                            yl]-5-nitro-2-furamide                      405 N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4- 361 25.0                    thiadiazol-2-yl}-1-benzothiophene-2-carboxamide                               406 N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2- 377 25.0                                             yl)-4-(trifluoromethyl)benzamide                                              407 tert-butyl 3-[(5-{[4-(trifluoromet                                        hyl)benzoyl]amino}-1,3,4- 417 25.0                                               thiadiazol-2-yl)amino]propanoate                                              408 N-{5-[(2-anilinoethyl)amino]-1,3,4                                        -thiadiazol-2-yl}-3,4- 408 24.9                                                  dichlorobenzamide                           409 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 443                                            24.9                                           triisopropylbenzamide                                                         410 2,6-dichloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 443 24.9                                                 yl]benzamide                                411 3-nitro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 370 24.8                  yl]benzamide                                                                  412 N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2- 362 24.7                                               yl)-1-benzothiophene-2-carboxamide                                            413 3-nitro-N-{5-[(4-phenylbutyl)amino                                        ]-1,3,4-thiadiazol-2- 398 24.7                                                   yl}benzamide                                414 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 385 24.7                    thiadiazol-2-yl}-2-methoxybenzamide                                           415 4-iodo-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide 451                                            24.6                                          416 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2,4- 415                                            24.5                                           difluorobenzamide                                                             417 3,4-dichloro-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 380 24.4                                                  thiadiazol-2-yl}benzamide                   418 3,4-dichloro-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2- 385 24.4                                             yl]benzamide                                419 4-bromo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 426 24.3                                                1,3,4-thiadiazol-2-yl)benzamide                                               420 tert-butyl 3-({5-[(3,4-dichloroben                                        zoyl)amino]-1,3,4- 417 24.1                    thiadiazol-2-yl}amino)propanoate                                              421 (E)-3-phenyl-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 338 24.0                                                  thiadiazol-2-yl}-2-propenamide                                                422 (E)-3-(2-chlorophenyl)-N-(5-{[3-(4                                        -methylpiperazino)- 421 24.0                   propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide                            423 2,4-difluoro-N-{5-[(4-fluorobenzyl)amino]-1,3,4- 365 23.8                   thiadiazol-2-yl}benzamide                                                     424 2,4,6-triisopropyl-N-{5-[(2-thienylmethyl)amino]-1,3,4- 443 23.6                                              thiadiazol-2-yl}benzamide                   425 4-iodo-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2- 443 23.5                                             yl}benzamide                                426 tert-butyl 3-[(5-{[(E)-3-(2-chlorophenyl)-2-propenoyl]- 409 23.5                                              amino}-1,3,4-thiadiazol-2-yl)amino]pr                                        opanoate                                      427 2,4-difluoro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]- 382 23.4                                                 amino}-1,3,4-thiadiazol-2-yl)benzamid                                        e                                             428 2-methoxy-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 381 23.3                                             1,3,4-thiadiazol-2-yl]benzamide                                               429 2-methoxy-N-{5-[(4-phenylbutyl)ami                                        no]-1,3,4-thiadiazol-2- 383 23.2                                                 yl}benzamide                                430 4-iodo-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2- 457                                             23.1                                           yl)benzamide                                                                  431 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2- 411 23.1                                             ethoxy-1-naphthamide                        432 (E)-3-phenyl-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4- 344 23.0                                            thiadiazol-2-yl)-2-propenamide                                                433 N-{5-[(cyclohexylmethyl)amino]-1,3                                        ,4-thiadiazol-2-yl}-2,4- 353 22.9                                                difluorobenzamide                           434 N-{5-[(2-anilioethyl)amino]-1,3,4-thiadiazol-2-yl}-4- 420 22.8                                                bromobenzamide                              435 N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 400 22.8                                             triisopropylbenzamide                       436 N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2- 416 22.8                                                yl}-3-nitrobenzamide                        437 3,5-difluoro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 361 22.7                                               yl]benzamide                                438 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6- 408 22.6                                             dichlorobenzamide                           439 (E)-3-(2-chlorophenyl)-N-{5-[(cyclohexylmethyl)amino]- 377 22.5                                               1,3,4-thiadiazol-2-yl}-2-propenamide        440 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]- 483 22.5                                                   methyl}amino)-1,3,4-thiadiazol-2-yl]-                                        2,4,6-                                         triisopropylbenzamide                                                         441 2,4,6-triisopropyl-N-[5-(undecylamino)-1,3,4- 501 22.5                      thiadiazol-2-yl]benzamide                                                     442 N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 427 22.3                                            triisopropylbenzamide                       443 (E)-3-(2-chlorophenyl)-N-{5-[(1-naphthylmethyl)amino]-1,3,4- --                                             22.1                                           thiadiazol-2-yl]-2propenamide                                                 444 N-(5-{[2-(dimethylamino)ethyl]amino}-1,3,4-thiadiazol-2- 418 21.9                                             yl)-2,4,6-triisopropylbenzamide                                               445 2,4-difluoro-N-(5-{]2-(2-thienyl)e                                        thyl]amino]-1,3,4- 367 21.9                    thiadiazol-2-yl)benzamide                                                     446 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 472 21.8                    thiadiazol-2-yl)-4-(trifluoromethyl)benzamide                                 447 3,4-dichloro-N-(5-{[2-(ethylsulfanyl)ethyl]amino]- 377 21.6                                                   1,3,4-thiadiazol-2-yl)benzamide                                               448 2,6-dichloro-N-(5-{[2-(1H-imidazol                                        -4-yl)ethyl]amino}- 383 21.6                   1,3,4-thiadiazol-2-yl)benzamide                                               449 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4- 331 21.5                                             methylbenzamide                             450 2-ethoxy-N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4- 399 21.4                                             thiadiazol-2-yl}-1-naphthamide                                                451 3,5-difluoro-N-{5-[(4-fluorobenzyl                                        )amino]-1,3,4- 365 21.4                        thiadiazol-2-yl}benzamide                                                     452 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2- 409 21.3                                                 yl}-2-methoxybenzamide                      453 N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 390 21.2                                            benzothiophene-2-carboxamide                                                  454 N-(5-{[2-(1H-imidazol-4-yl)ethyl]a                                        mino}-1,3,4- 441 21.2                          thiadiazol-2-yl)-4-iodobenzamide                                              455 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- 472 20.8                                             yl}-4-bromobenzamide                        456 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- 429 20.8                                             yl}-5-nitro-2-furamide                      457 4-methyl-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 375 20.7                     thiadiazol-2-yl}benzamide                                                     458 3,5-difluoro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 400 20.7                                             thiadiazol-2-yl)benzamide                   459 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 481 20.7                    thiadiazol-2-yl}-4-iodobenzamide                                              460 4-[({5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- 476 20.7         yl}amino)carbonyl]benzenesulfonyl fluoride                                    461 3,4-dichloro-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2- 401                                             20.6                                           yl}benzamide                                                                  462 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3- 424 20.5         nitrobenzamide                                                                463 N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2- 400 20.3                                               yl)-2-ethoxy-1-naphthamide                  464 4-cyano-N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2- 359                                             20.3                                           yl}benzamide                                                                  465 (E)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-3- 287 20.2                                                phenyl-2-propenamide                        466 N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2- 365 20.1                                             yl)-1-benzothiophene-2-carboxamide                                            467 4-iodo-N-(5-{[2-)4-methylpiperazin                                        o)propyl]amino}- 487 20.1                      1,3,4-thiadiazol-2-yl)benzamide                                               468 3,5-difluoro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 387                                             20.1                                           1,3,4-thiadiazol-2-yl]benzamide                                               469 N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2- 379 20.1                                                  yl}-3-nitrobenzamide                        470 N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2 401 20.0                                                   yl}-4-iodobenzamide                         471 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 380 20.0                    thiadiazol-2-yl}-4-cyanobenzamide                                             472 4-({[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]amino}- 407 20.0                                                carbonyl)benzenesulfonyl fluoride         __________________________________________________________________________ 

We claim:
 1. A compound of formula I ##STR16## or pharmaceutically acceptable salts thereof wherein: Y isa) --NHR₁, or ##STR17## X is a) --O--, b) --S(═O)_(h) --, c) --CH₂ --, or d) --NR₂ --; R₁ isa) C₄₋₁₂ alkyl, b) --(CH₂)_(i) -C₃₋₇ cycloalkyl, c) 6,6-dimethylbicyclo[3.1.1]-2-heptyl, d) --(CH₂)_(j) -M, e) --(CH₂)_(j) -W, f) --(CH₂)_(k) aryl, wherein aryl may be substituted with one to three R₃, g) --(CH₂)_(k) -het, wherein het may be substituted with one to three R₃, or h) --(CH₂)_(k) -Q, wherein Q may be substituted with one to three R₃ ; R₂ isa) H, b) C₁₋₄ alkyl, c) --C(═O)C₁₋₄ alkyl, d) --S(═O)C₁₋₄ alkyl, e) --CO₂ C₁₋₄ alkyl, or f) --CO₂ CH₂ phenyl; R₃ isa) halo, b) C₁₋₄ alkyl, c) C₁₋₄ alkoxy, d) benzyl, e) --CN, f) --SO₂ F, g) --SO₂ NH₂, h) --CF₃, i) --NO₂, j) --OCH₂ O--, k) --CO₂ (C₁₋₄ alkyl), l) --C(═O)C₁₋₄ alkyl, m) --C(═O)NH₂, n) --NHCO₂ (C₁₋₄ alkyl), or o) --C(═O)--O--C(═O)--; M isa) --CN, b) halo, c) --CO₂ C₁₋₄ alkyl, d) --CH(phenyl)₂, ##STR18## W is a) --OR₄, b) --SR₄, c) --NHR₅, or d) --NR₆ R₇ ; R₄ isa) C₁₋₄ alkyl, b) C₃₋₇ cycloalkyl, or c) aryl; R₅ isa) C₁₋₄ alkyl, b) C₃₋₇ cycloalkyl, c) aryl, or d) --C(═O)C₁₋₄ alkyl; R₆ and R₇ are independentlya) C₁₋₄ alkyl, or b) R₆ and R₇ together with nitrogen form azetidinyl, pyrrolidinyl, piperdinyl, piperazinyl, 4-methyl-1-piperazinyl, hydantoin, 4-morpholinyl, thiomorpholinyl, or 2-oxo-1-pyrrolidinyl; R₁ isa) C₁₋₁₈ alkyl, b) C₂₋₁₈ alkenyl, c) C₂₋₁₈ alkynyl, d) C₂₋₆ alkyl substituted with one to three halo, C₁₋₃ alkoxy, --OH, --SH, or --CO₂ H, e) C₂₋₆ alkenyl substituted with aryl, wherein the aryl may be in turn substituted with one to three R₂, f) --(CH₂)_(i) aryl, wherein aryl may be substituted with one to three R₃, g) --(CH₂)_(i) -Q, wherein Q may be substituted with one to three R₃, or h) --(CH₂)_(i) -U, wherein U may be substituted with one to three R₃ ; aryl is phenyl or naphthyl; het isa) furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, b) pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl, c) indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, isoindolyl, or d) quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl or cinnolinyl; U isa) furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, b) pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl, or c) indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, isoindolyl; Q isa) 2-, 3-, or 4-piperidinyl, b) 1-, or 2-pyrrolidinyl, wherein the nitrogen atom in a) and b) may be substituted with C₁₋₄ alkyl, phenyl, benzyl, or --C(═O)C₁₋₄ alkyl, c) morpholinyl, d) thiomorpholinyl, e) dioxolanyl, f) imidazolidinyl, g) oxathiolanyl, h) oxazolidinyl, i) tetrahydrofuryl, or j) 2-oxo-1-pyrrolidinyl. h is 0, 1, or 2; i is 0, 1, 2, 3, or 4; j is 2, 3, or 4; k is 0, 1, 2, 3, 4, 5, or 6; and with the following provisos:a) where R₃ is phenyl or 4-methoxyphenyl, R₁ is other than phenyl, 4-methoxyphenyl, or 4-chlorophenyl; b) where R₃ is --CH₂ phenyl, R₁ is other than phenyl or --CH₂ phenyl; c) where R₃ is H, substituted or unsubstituted alkyl or phenyl, R₁ is other than unsubstituted alkyl or phenyl.
 2. A compound of claim 1 wherein X isa) --O--, or b) --NR₂ --;R₂ is a) H, b) --CO₂ C₁₋₄ alkyl, or c) --CO₂ CH₂ phenyl.
 3. A compound of claim 1 wherein het is furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, isoxazolyl, pyridyl, benzothienyl, or indolyl.
 4. A compound of claim 1 wherein Q is 1-methyl-2-pyrrolidinyl, 1-methyl-4-piperidinyl, 1-ethylcarboxylate-4-piperidinyl, 1-benzyl-4-piperidinyl, or tetrahydrofuryl.
 5. A compound of claim 1 wherein R₃ isa) chloro, b) fluoro, c) methyl, d) methoxy, e) ethoxy, f) --CN, g) --SO₂ NH₂, h) --NO₂, i) --OCH₂ O--, or j) --C(═O)--O--C(═O)--.
 6. A compound of claim 1 wherein Rx isa) C₂₋₁₈ alkenyl, b) C₂₋₆ alkyl substituted with halo, or --CO₂ H, c) C₂₋₆ alkenyl substituted with aryl, wherein the aryl may be in turn substituted with one to three halo, d) --(CH₂)_(i) aryl, wherein aryl may be substituted with one to three R₃, or e) --(CH₂)_(i) -U, wherein het may be substituted with one to three R₃ ; Y is --NHR₁ ; aryl, U, R₁ and i are the same as defined in claim 1; and R₃ is chloro, fluoro, methyl, methoxy, ethoxy, --CN, --SO₂ NH₂, --NO₂, --OCH₂ O--, or --C(═O)--O--C(═O)--.
 7. A compound of claim 1 which is1) 2-methoxy-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide, 2) 4-methyl-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide, 3) 5-chloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]pentanamide, 4) 4-cyano-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide, 5) 3-nitro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide, 6) 3,5-difluoro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide, 7) (E)-3-(2-chlorophenyl)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 8) 2-ethoxy-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-1-naphthamide, 9) (E)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 10) 2,6-dichloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide, 11) 3,4-dichloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide, 12) (E)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-3-phenyl-2-propenamide, 13) 4-iodo-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide, 14) 1,3-dioxo-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide, 15) 4-({[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]amino}carbonyl)benzenesulfonyl fluoride, 16) 5-nitro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-2-furamide, 17) (E)-3-(2-chlorophenyl)-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 18) 2-ethoxy-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide, 19) (E)-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 20) 2,6-dichloro-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 21) 3,4-dichloro-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 22) N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide, 23) N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide, 24) N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 25) 2,4-difluoro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 26) 4-bromo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 27) 4-methyl-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 28) 5-chloro-N-(5-[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)pentanamide, 29) 4-cyano-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 30) 3-nitro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 31) 3,5-difluoro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 32) (E)-3-(2-chlorophenyl)-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 33) 3,4-dichloro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 34) (E)-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 35) 4-iodo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 36) 1,3-dioxo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dihydro-2-benzofuran-5-carboxamide, 37) 4-{[(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride, 38) 2,4,6-triisopropyl-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 39) 5-nitro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-furamide, 40) N-(5-[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 41) (E)-3-(2-chlorophenyl)-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 42) 2-ethoxy-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl-1-naphthamide, 43) (E)-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 44) 2,6-dichloro-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 45) (E)-3-phenyl-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 46) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide, 47) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-4-bromobenzamide, 48) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-4-methylbenzamide, 49) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide, 50) (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-(2-chlorophenyl)-2-propenamide, 51) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide 52) (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 53) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6-dichlorobenzamide, 54) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3,4-dichlorobenzamide, 55) (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 56) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide, 57) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 58) 4-[({5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride, 59) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide 60) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide, 61) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 62) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-methoxybenzamide, 63) 4-bromo-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 64) 5-chloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)pentanamide, 65) 4-cyano-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 66) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-nitrobenzamide, 67) 3,5-difluoro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 68) (E)-3-(2-chlorophenyl)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 69) 2-ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide, 70) (E)-N-(5-[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 71) 2,6-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 72) 3,4-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 73) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4(trifluoromethyl)benzamide, 74) (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 75) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide, 76) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 77) 4-[(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride, 78) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide, 79) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-5-nitro-2-furamide, 80) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 81) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide, 82) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-4-methylbenzamide, 83) 5-chloro-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]pentanamide, 84) 4-cyano-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]benzamide, 85) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-3-nitrobenzamide, 86) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-3,5-difluorobenzamide, 87) (E)-3-(2-chlorophenyl)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 88) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide, 89) (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 90) 2,6-dichloro-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]benzamide, 91) 3,4-dichloro-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]benzamide, 92) (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-3-phenyl-2-propenamide, 93) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-4-iodobenzamide, 94) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 95) 4-({[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]amino}carbonyl)benzenesulfonyl fluoride, 96) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2,4,6-triisopropylbenzamide, N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-5-nitro-2-furamide, 97) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide, 98) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide, 99) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide, 100) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-methylbenzamide, 101) 5-chloro-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide, 102) 4-cyano-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 103) (E)-3-(2-chlorophenyl)-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 104) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 105) (E)-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide 106) 3,4-dichloro-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 107) (E)-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 108) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 109) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropyl benzamide, 110) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide, 111) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide, 112) 5-chloro-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]pentanamide, 113) 4-cyano-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]benzamide, 114) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-3,5-difluorobenzamide, 115) (E)-3-(2-chlorophenyl)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 116) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide, 117) (E)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 118) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 119) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2,4,6-triisopropylbenzamide, 120) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-5-nitro-2-furamide, 121) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide, 122) (E)-3-(2-chlorophenyl)-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 123) (E)-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 124) 2-6-dichloro-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 125) (E)-3-phenyl-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 126) 2,4,6-triisopropyl-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 127) 2-ethoxy-N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide, 128) (E)-N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 129) N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 130) (E)-3-(2-chlorophenyl)-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 131) 2,6-dichloro-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 132) 3,4-dichloro-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 133) (E)-3-phenyl-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 134) 4-iodo-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 135) 1,3-dioxo-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide, 136) 2,4,6-triisopropyl-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 137) N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 138) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide, 139) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide, 140) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-bromobenzamide, 141) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-methylbenzamide, 142) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-5-chloropentanamide, 143) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-cyanobenzamide, 144) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3,5-difluorobenzamide, 145) (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-(2-chlorophenyl)-2-propenamide, 146) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 147) (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 148) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6-dichlorobenzamide, 149) (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 150) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide, 151) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 152) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide, 153) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 154) 4-cyano-N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 155) N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide, 156) (E)-N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 157) N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 158) 2,4-difluoro-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 159) 2-methoxy-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 160) 4-methyl-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 161) 5-chloro-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide, 162) 4-cyano-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 163) N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide, 164) 3,5-difluoro-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 165) (E)-3-(2-chlorophenyl)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 166) 2-ethoxy-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide, 167) (E)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide 168) 2,6-dichloro-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 169) (E)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 170) 4-iodo-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 171) N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 172) 4-[({5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride, 173) 2,4,6-triisopropyl-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 174) N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide, 175) N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 176) 2,4-difluoro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 177) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide, 178) 5-chloro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide, 179) 4-cyano-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 180) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide, 181) 3,5-difluoro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 182) (E)-3-(2-chlorophenyl)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 183) 2-ethoxy-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide 184) (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 185) 2,6-dichloro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 186) (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 187) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 188) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide, 189) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide 190) 2-ethoxy-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide, 191) (E)-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 192) 2,6-dichloro-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 193) 3,4-dichloro-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 194) (E)-3-phenyl-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 195) 2,4,6-triisopropyl-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 196) N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 197) 2,4,6-triisopropyl-N-{5-[(2-piperidinoethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 198) (E)-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 199) 2,6-dichloro-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 200) 3,4-dichloro-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 201) N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 202) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-2-methoxybenzamide, 203) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-bromobenzamide, 204) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-methylbenzamide, 205) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-5-chloropentanamide, 206) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-cyanobenzamide, 207) (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-3-(2-chlorophenyl)-2-propenamide, 208) N-(5-{[4-(aminosulfonyl)phenethyl]amino}1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide, 209) (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 210) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-2,6-dichlorobenzamide, 211) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-3,4-dichlorobenzamide, 212) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-(trifluoromethyl)benzamide, 213) (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 214) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide, 215) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 216) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide, 217) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 218) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2,4-difluorobenzamide, 219) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-methoxybenzamide, 220) 4-bromo-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 221) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-4-methylbenzamide, 222) 4-cyano-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 223) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-nitrobenzamide, 224) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3,5-difluorobenzamide, 225) (E)-3-(2-chlorophenyl)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 226) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide, 227) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 228) 2,6-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 229) 3,4-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 230) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-4-(trifluoromethyl)benzamide, 231) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 232) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide, 233) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 234) 4-{[(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride, 235) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide, 236) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-5-nitro-2-furamide, 237) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 238) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide, 239) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide 240) 4-cyano-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 241) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide, 242) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 243) (E)-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 244) 2,6-dichloro-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 245) (E)-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 246) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 247) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide 248) 4-cyano-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 249) N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide, 250) N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 251) (E)-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 252) 2,6-dichloro-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 253) N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide, 254) N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 255) 2,4-difluoro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 256) 2-methoxy-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 257) 4-bromo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 258) 4-methyl-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 259) 5-chloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide, 260) 4-cyano-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 261) 3-nitro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 262) 3,5-difluoro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 263) (E)-3-(2-chlorophenyl)-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 264) 2-ethoxy-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide, 265) (E)-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 266) 2,6-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 267) 3,4-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 268) N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-4-(trifluoromethyl) benzamide, 269) (E)-3-phenyl-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 270) 4-iodo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 271) 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide, 272) 4-[({5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride, 273) 2,4,6-triisopropyl-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 274) 5-nitro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-2-furamide, 275) N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 276) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide, 277) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide, 278) 4-bromo-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 279) 5-chloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide 280) 4-cyano-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 281) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-3,5-difluorobenzamide, 282) (E)-3-(2-chlorophenyl)-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 283) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 284) (E)-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 285) 2,6-dichloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 286) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 287) 4-[({5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride, 288) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropyl benzamide, 289) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide, 290) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 291) 2,4-difluoro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 292) 4-bromo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 293) 4-methyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 294) 5-chloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]pentanamide, 295) 4-cyano-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 296) 3-nitro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 297) 3,5-difluoro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 298) (E)-3-(2-chlorophenyl)-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 299) 2-ethoxy-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1-naphthamide, 300) (E)-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 301) 2,6-dichloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 302) 3,4-dichloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 303) 4-(trifluoromethyl)-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 304) (E)-3-phenyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 305) 4-iodo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 306) 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide, 307) 4-({[5-(undecylamino)-1,3,4-thiadiazol-2-yl]amino}carbonyl)benzenesulfonyl fluoride, 308) 2,4,6-triisopropyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide, 309) 5-nitro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-2-furamide, 310) N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide, 311) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide, 312) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide 313) 4-bromo-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl benzamide, 314) 5-chloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide, 315) 4-cyano-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 316) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide, 317) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-3,5-difluorobenzamide, 318) (E)-3-(2-chlorophenyl)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 319) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 320) (E)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 321) 2,6-dichloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 322) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-4-(trifluoromethyl) benzamide, 323) (E)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 324) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide, 325) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 326) 4-[({5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride, 327) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide, 328) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide 329) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 330) 2,4-difluoro-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 331) 4-cyano-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 332) 3-nitro-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 333) (E)-3-(2-chlorophenyl)-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 334) 2-ethoxy-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide, 335) (E)-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 336) 2,6-dichloro-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 337) (E)-3-phenyl-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 338) 4-iodo-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 339) 1,3-dioxo-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dihydro-2-benzofuran-5-carboxamide, 340) 2,4,6-triisopropyl-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 341) N-(5-{[2-(2-thienyl)ethyl]amino-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 342) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3-(2-chlorophenyl)-2-propenamide, 343) N-(5-[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide, 344) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 345) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2,6-dichlorobenzamide, 346) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3,4-dichlorobenzamide, 347) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-4-(trifluoromethyl)benzamide, 348) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 349) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide, 350) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide, 351) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 352) (E)-3-(2-chlorophenyl)-N-(5-{[3-(4-methylpiperazino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 353) (E)-N-(5-{[3-(4-methylpiperazino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 354) 4-iodo-N-(5-{[3-(4-methylpiperazino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 355) (E)-N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 356) 2,6-dichloro-N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 357) N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide, 358) 2,4-difluoro-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 359) 4-bromo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 360) 5-chloro-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)pentanamide, 361) (E)-3-(2-chlorophenyl)-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 362) 2-ethoxy-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide, 363) (E)-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 364) (E)-3-phenyl-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 365) 4-iodo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 366) 1,3-dioxo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dihydro-2-benzofuran-5-carboxamide, 367) 4-cyano-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 368) (E)-3-(2-chlorophenyl)-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 369) 2-ethoxy-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide, 370) (E)-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 371) 2,6-dichloro-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide 372) 4-iodo-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 373) 1,3-dioxo-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide, 374) 2,4,6-triisopropyl-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 375) N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 376) N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide, 377) (E)-N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 378) (E)-N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 379) N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 380) N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide, 381) N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 382) 4-bromo-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 383) (E)-3-(2-chlorophenyl)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 384) 2-ethoxy-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide, 385) (E)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 386) 2,6-dichloro-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 387) 3,4-dichloro-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 388) (E)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 389) N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide, 390) N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide, 391) tert-butyl 3-[(5-{[(E)-3-(2-chlorophenyl)-2-propenoyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate, 392) tert-butyl 3-[(5-{[(2-ethoxy-1-naphthyl)carbonyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate, 393) tert-butyl 3-({5-[(E)-9-octadecenoylamino]-1,3,4-thiadiazol-2-yl}amino)propanoate, 394) tert-butyl 3-({5-[(2,6-dichlorobenzoyl)amino]-1,3,4-thiadiazol-2-yl}amino)propanoate, 395) tert-butyl 3-({5-[(3,4-dichlorobenzoyl)amino]-1,3,4-thiadiazol-2-yl}amino)propanoate, 396) tert-butyl 3-[(5-{[4-(trifluoromethyl)benzoyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate, 397) tert-butyl 3-[(5-1-[(E)-3-phenyl-2-propenoyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate, 398) tert-butyl 3-[(5-{[(1,3-dioxo-1,3-dihydro-2-benzofuran-5-yl)carbonyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate, 399) tert-butyl 3-({5-[(2,4,6-triisopropylbenzoyl)amino]-1,3,4-thiadiazol-2-yl}amino)propanoate, 400) (E)-3-(2-chlorophenyl)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 401) N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide, 402) (E)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 403) (E)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-3-phenyl-2-propenamide, 404) N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide, 405) (E)-3-(2-chlorophenyl)-N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide, 406) N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 407) (E)-N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 408) N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide, 409) (E)-3-(2-chlorophenyl)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 410) 2-ethoxy-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide, 411) (E)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 412) 2,6-dichloro-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 413) (E)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 414) N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide, 415) N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide, 415) N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 416) 4-bromo-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 417) (E)-3-(2-chlorophenyl)-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide, 418) 2-ethoxy-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide, 419) (E)-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 420) 2,6-dichloro-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 421) 3,4-dichloro-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 422) N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4(trifluoromethyl)benzamide, 423) (E)-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 424) N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide, 425) N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide, 426) (E)-3-(2-chlorophenyl)-N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 427) N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide, 428) (E)-N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 429) (E)-N-(5-{[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 430) 2,4,6-triisopropyl-N-(5-{[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 431) N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-3-nitrobenzamide, 432) N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide, 433) (E)-N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 434) 2,6-dichloro-N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]benzamide, 435) N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 436) N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-5-nitro-2-furamide, 437) (E)-3-(2-chlorophenyl)-N-[5-(neopentylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 438) 2-ethoxy-N-[5-(neopentylamino)-1,3,4-thiadiazol-2-yl]-1-naphthamide, 439) 2,6-dichloro-N-[5-(neopentylamino)-1,3,4-thiadiazol-2-yl]benzamide, 440) 2-methoxy-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]benzamide, 441) 3-nitro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]benzamide, 442) 3,5-difluoro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]benzamide, 443) (E)-3-(2-chlorophenyl)-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide, 444) 2-ethoxy-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-1-naphthamide, 445) (E)-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 446) 2,6-dichloro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]benzamide, 447) 1,3-dioxo-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide, 448) 5-nitro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-2-furamide, 449) N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide, 450) ethyl 4-[(5-{[(E)-3-(2-chlorophenyl)-2-propenoyl]amino}-1,3,4-thiadiazol-2-yl)amino]tetrahydro-1(2H)-pyridinecarboxylate, 451) ethyl 4-[(5-{[(2-ethoxy-1-naphthyl)carbonyl]amino}-1,3,4-thiadiazol-2-yl)amino]tetrahydro-1(2H)-pyridinecarboxylate, 452) ethyl 4-({5-[(E)-9-octadecenoylamino]-1,3,4-thiadiazol-2-yl}amino)tetrahydro-1(2H)-pyridinecarboxylate, 453) ethyl 4-({5-[(2,6-dichlorobenzoyl)amino]-1,3,4-thiadiazol-2-yl}amino)tetrahydro-1(2H)-pyridinecarboxylate, 454) ethyl 4-({5-[(1-benzothiophen-2-ylcarbonyl)amino]-1,3,4-thiadiazol-2-yl}amino)tetrahydro-1(2H)-pyridinecarboxylate, 455) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-4-bromobenzamide, 456) (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-3-(2-chlorophenyl)-2-propenamide, 457) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 458) (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 459) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-2,6-dichlorobenzamide, 460) (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide, 461) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide, 462) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 463) 4-[({5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- yl}amino)carbonyl]benzenesulfonyl fluoride, 464) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide, 465) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide, 466) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide, 467) (E)-N-(5-{[2-(dimethylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, or 468) N-(5-{[2-(dimethylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide.
 8. A compound of claim 1 which is1) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide, 2) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 3) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 4) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 5) 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide, 6) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 7) 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide, 8) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 9) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 10) 2-ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide, 11) 2,6-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 12) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide, 13) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide, 14) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 15) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide, 16) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 17) 2,6-dichloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 18) 2,6-dichloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 19) (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 20) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2,6-dichlorobenzamide, 21) 2,6-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 22) 4-cyano-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, 23) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 24) 4-cyano-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 25) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-5-nitro-2-furamide, 26) 2,6-dichloro-N-[5-{[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]benzamide, 27) 4-cyano-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide, 28) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 29) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6dichlorobenzamide, 30) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide, 31) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide, 32) (E)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 33) (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, 34) (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide, 35) (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide, 36) 2,6-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, or 37) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide.
 9. A compound of claim 1 which is1) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide, 2) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 3) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 4) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 5) 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide, 6) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 7) 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide, 8) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, or 9) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide.
 10. A pharmaceutical composition which comprises an effective amount of the compound of claim 1 to treat cytomegalovirus infection and a pharmaceutically acceptable carrier.
 11. A method for treating viral infections in a mammal comprising administering to said mammal in need thereof an effective amount of a compound of formula I of claim
 1. 12. A method of claim 11 wherein said effective amount of a compound of formula is administered orally, parenterally or topically in a pharmaceutical composition.
 13. A method of claim 11 wherein said viral infection is human cytomegalovirus infection.
 14. A method of claim 11 wherein said effective amount of a compound of formula is administered in an amount of from about 0.1 to 300 mg/kg of mammal body weight. 